#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/88/7218832.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_7218832
loop_
_publ_author_name
'Chen, Ying-Hsuan'
'Peng, Kai-En'
'Lee, Gene-Hsiang'
'Peng, Shie-Ming'
'Chiu, Ching-Wen'
_publ_section_title
;
 Symmetrical non-chelating poly-N-heterocyclic carbenes
;
_journal_issue                   107
_journal_name_full               'RSC Adv.'
_journal_page_first              62789
_journal_paper_doi               10.1039/C4RA12597E
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C19 H18 I N3 O2'
_chemical_formula_weight         447.26
_chemical_name_systematic        '[5]I'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.356(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4332(10)
_cell_length_b                   8.5362(6)
_cell_length_c                   15.4137(11)
_cell_measurement_reflns_used    4801
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.69
_cell_volume                     1868.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13991
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_T_max  0.8063
_exptl_absorpt_correction_T_min  0.6715
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile, ether'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.229
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.216
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.2929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3781
_reflns_number_total             4273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra12597e2.cif
_cod_data_source_block           ic16325
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7218832
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.554862(17) 1.31374(3) 1.177630(15) 0.02909(10) Uani 1 1 d .
O1 O 0.16270(18) 0.4254(3) 0.86239(19) 0.0355(6) Uani 1 1 d .
O2 O -0.0350(2) 0.8130(3) 0.9249(2) 0.0448(8) Uani 1 1 d .
N1 N 0.4100(2) 0.8337(3) 1.07732(19) 0.0230(6) Uani 1 1 d .
N2 N 0.3147(2) 1.0165(3) 1.10739(18) 0.0226(6) Uani 1 1 d .
N3 N 0.0439(2) 0.5992(3) 0.8802(2) 0.0274(7) Uani 1 1 d .
C1 C 0.4036(2) 0.9663(4) 1.1207(2) 0.0233(7) Uani 1 1 d .
H1 H 0.4551 1.0182 1.1563 0.028 Uiso 1 1 calc R
C2 C 0.3207(3) 0.7904(4) 1.0355(2) 0.0221(7) Uani 1 1 d .
C3 C 0.2890(2) 0.6597(4) 0.9843(2) 0.0218(7) Uani 1 1 d .
H3 H 0.3298 0.5783 0.9722 0.026 Uiso 1 1 calc R
C4 C 0.1937(3) 0.6593(4) 0.9528(2) 0.0239(7) Uani 1 1 d .
C5 C 0.1332(2) 0.7790(4) 0.9701(2) 0.0239(7) Uani 1 1 d .
C6 C 0.1633(2) 0.9086(4) 1.0209(2) 0.0256(7) Uani 1 1 d .
H6 H 0.1220 0.9897 1.0323 0.031 Uiso 1 1 calc R
C7 C 0.2596(2) 0.9096(4) 1.0540(2) 0.0227(7) Uani 1 1 d .
C8 C 0.1370(3) 0.5426(4) 0.8942(2) 0.0268(7) Uani 1 1 d .
C9 C 0.0370(3) 0.7405(5) 0.9248(2) 0.0320(8) Uani 1 1 d .
C10 C -0.0352(3) 0.5262(5) 0.8259(2) 0.0299(8) Uani 1 1 d .
C11 C -0.0569(3) 0.3728(5) 0.8406(3) 0.0381(10) Uani 1 1 d .
H11 H -0.0183 0.3130 0.8850 0.046 Uiso 1 1 calc R
C12 C -0.1365(4) 0.3066(5) 0.7891(3) 0.0484(13) Uani 1 1 d .
H12 H -0.1517 0.2000 0.7974 0.058 Uiso 1 1 calc R
C13 C -0.1934(3) 0.3953(7) 0.7261(3) 0.0500(12) Uani 1 1 d .
H13 H -0.2486 0.3502 0.6924 0.060 Uiso 1 1 calc R
C14 C -0.1708(3) 0.5489(6) 0.7117(3) 0.0450(11) Uani 1 1 d .
H14 H -0.2097 0.6091 0.6677 0.054 Uiso 1 1 calc R
C15 C -0.0912(3) 0.6147(5) 0.7616(3) 0.0370(9) Uani 1 1 d .
H15 H -0.0749 0.7203 0.7518 0.044 Uiso 1 1 calc R
C16 C 0.4945(3) 0.7328(4) 1.0833(2) 0.0281(8) Uani 1 1 d .
H16A H 0.4942 0.6822 1.0255 0.034 Uiso 1 1 calc R
H16B H 0.4917 0.6491 1.1272 0.034 Uiso 1 1 calc R
C17 C 0.5852(3) 0.8233(5) 1.1094(3) 0.0364(9) Uani 1 1 d .
H17A H 0.5856 0.9124 1.0695 0.055 Uiso 1 1 calc R
H17B H 0.6387 0.7546 1.1058 0.055 Uiso 1 1 calc R
H17C H 0.5899 0.8614 1.1700 0.055 Uiso 1 1 calc R
C18 C 0.2811(3) 1.1586(4) 1.1474(3) 0.0292(8) Uani 1 1 d .
H18A H 0.3276 1.1889 1.2000 0.035 Uiso 1 1 calc R
H18B H 0.2208 1.1352 1.1668 0.035 Uiso 1 1 calc R
C19 C 0.2671(3) 1.2935(4) 1.0828(3) 0.0387(10) Uani 1 1 d .
H19A H 0.3269 1.3178 1.0642 0.058 Uiso 1 1 calc R
H19B H 0.2451 1.3856 1.1112 0.058 Uiso 1 1 calc R
H19C H 0.2201 1.2644 1.0312 0.058 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
C1 N1 C2 108.6(3)
C1 N1 C16 126.6(3)
C2 N1 C16 124.1(3)
C1 N2 C7 108.3(3)
C1 N2 C18 125.2(3)
C7 N2 C18 126.4(3)
C9 N3 C8 111.8(3)
C9 N3 C10 122.8(3)
C8 N3 C10 125.4(3)
N1 C1 N2 110.4(3)
N1 C2 C3 131.3(3)
N1 C2 C7 106.1(3)
C3 C2 C7 122.6(3)
C4 C3 C2 114.0(3)
C3 C4 C5 123.3(3)
C3 C4 C8 128.5(3)
C5 C4 C8 108.1(3)
C6 C5 C4 123.4(3)
C6 C5 C9 128.3(3)
C4 C5 C9 108.3(3)
C5 C6 C7 113.8(3)
N2 C7 C6 130.7(3)
N2 C7 C2 106.5(3)
C6 C7 C2 122.8(3)
O1 C8 N3 125.4(3)
O1 C8 C4 129.0(3)
N3 C8 C4 105.6(3)
O2 C9 N3 125.3(3)
O2 C9 C5 128.4(4)
N3 C9 C5 106.3(3)
C11 C10 C15 121.1(4)
C11 C10 N3 120.0(4)
C15 C10 N3 118.8(4)
C10 C11 C12 118.8(4)
C13 C12 C11 120.3(4)
C14 C13 C12 120.4(4)
C13 C14 C15 119.7(4)
C14 C15 C10 119.7(4)
N1 C16 C17 112.5(3)
N2 C18 C19 111.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.201(4)
O2 C9 1.210(5)
N1 C1 1.326(4)
N1 C2 1.384(5)
N1 C16 1.482(5)
N2 C1 1.334(4)
N2 C7 1.381(4)
N2 C18 1.480(4)
N3 C9 1.400(5)
N3 C8 1.407(5)
N3 C10 1.432(4)
C2 C3 1.395(5)
C2 C7 1.408(5)
C3 C4 1.375(5)
C4 C5 1.399(5)
C4 C8 1.487(5)
C5 C6 1.380(5)
C5 C9 1.475(5)
C6 C7 1.393(5)
C10 C11 1.375(6)
C10 C15 1.386(6)
C11 C12 1.393(6)
C12 C13 1.380(7)
C13 C14 1.379(7)
C14 C15 1.381(6)
C16 C17 1.510(5)
C18 C19 1.511(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199512
