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#$Date: 2019-11-24 22:22:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/68/4516858.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_4516858
loop_
_publ_author_name
'Vellé, Alba'
'Cebollada, Andrea'
'Macías, Ramón'
'Iglesias, Manuel'
'Gil-Moles, María'
'Sanz Miguel, Pablo J.'
_publ_section_title
;
 From Imidazole toward Imidazolium Salts and N-Heterocyclic Carbene
 Ligands: Electronic and Geometrical Redistribution.
;
_journal_issue                   4
_journal_name_full               'ACS omega'
_journal_page_first              1392
_journal_page_last               1399
_journal_paper_doi               10.1021/acsomega.7b00138
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C23 H26 N4 O2, 2(I)'
_chemical_formula_sum            'C23 H26 I2 N4 O2'
_chemical_formula_weight         644.28
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.5830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   36.0917(15)
_cell_length_b                   5.1773(2)
_cell_length_c                   13.8210(6)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.26
_cell_volume                     2581.57(18)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15708
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.640
_diffrn_reflns_theta_min         2.258
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.461
_exptl_absorpt_correction_T_max  0.611
_exptl_absorpt_correction_T_min  0.437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       prisms
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0527P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0698
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2797
_reflns_number_total             3108
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao7b00138_si_004.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516858
_shelx_shelxl_version_number     2014/7
_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   0.480
_shelx_estimated_absorpt_t_max   0.639
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_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
I1 I 0.07791(2) 0.12453(2) 0.09847(2) 0.02668(7) Uani 1 1 d . . .
N1 N 0.02381(5) 0.6622(3) 0.30974(13) 0.0216(3) Uani 1 1 d . . .
C2 C 0.05990(5) 0.6123(3) 0.29544(15) 0.0214(4) Uani 1 1 d . . .
H2 H 0.0752 0.6939 0.2496 0.026 Uiso 1 1 calc R U .
N3 N 0.07015(4) 0.4278(3) 0.35729(12) 0.0208(3) Uani 1 1 d . . .
C4 C 0.04024(6) 0.3546(4) 0.41076(16) 0.0261(4) Uani 1 1 d . . .
H4 H 0.0401 0.2252 0.4595 0.031 Uiso 1 1 calc R U .
C5 C 0.01120(5) 0.5008(4) 0.38099(14) 0.0253(4) Uani 1 1 d . . .
H5 H -0.0133 0.4938 0.4046 0.030 Uiso 1 1 calc R U .
C6 C 0.10695(5) 0.3007(4) 0.36447(15) 0.0239(4) Uani 1 1 d . . .
H61 H 0.1135 0.2354 0.2998 0.029 Uiso 1 1 calc R U .
H62 H 0.1055 0.1508 0.4087 0.029 Uiso 1 1 calc R U .
C7 C 0.13707(5) 0.4818(4) 0.40129(16) 0.0274(4) Uani 1 1 d . . .
H71 H 0.1295 0.5677 0.4616 0.033 Uiso 1 1 calc R U .
H72 H 0.1603 0.3855 0.4148 0.033 Uiso 1 1 calc R U .
O8 O 0.14228(4) 0.6682(3) 0.32676(13) 0.0337(4) Uani 1 1 d . . .
C11 C 0.17234(6) 0.8288(4) 0.3372(2) 0.0388(6) Uani 1 1 d . . .
C12 C 0.17822(7) 0.9900(5) 0.2579(2) 0.0454(7) Uani 1 1 d . . .
H12 H 0.1623 0.9808 0.2021 0.055 Uiso 1 1 calc R U .
C13 C 0.20742(9) 1.1631(5) 0.2614(3) 0.0614(10) Uani 1 1 d . . .
H13 H 0.2115 1.2747 0.2082 0.074 Uiso 1 1 calc R U .
C14 C 0.23091(8) 1.1737(5) 0.3430(4) 0.0705(12) Uani 1 1 d . . .
H14 H 0.2511 1.2916 0.3452 0.085 Uiso 1 1 calc R U .
C15 C 0.22496(7) 1.0140(5) 0.4203(3) 0.0642(10) Uani 1 1 d . . .
H15 H 0.2411 1.0220 0.4757 0.077 Uiso 1 1 calc R U .
C16 C 0.19523(7) 0.8386(4) 0.4181(3) 0.0495(8) Uani 1 1 d . . .
H16 H 0.1911 0.7286 0.4717 0.059 Uiso 1 1 calc R U .
C21 C 0.0000 0.8278(5) 0.2500 0.0233(5) Uani 1 2 d S T P
H21 H -0.0148 0.9360 0.2900 0.028 Uiso 1 1 d R U .
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
C2 N1 C5 109.13(16) . .
C2 N1 C21 126.02(15) . .
C5 N1 C21 124.15(15) . .
N3 C2 N1 107.27(17) . .
N3 C2 H2 126.4 . .
N1 C2 H2 126.4 . .
C2 N3 C4 109.56(16) . .
C2 N3 C6 126.54(17) . .
C4 N3 C6 123.73(17) . .
C5 C4 N3 107.21(17) . .
C5 C4 H4 126.4 . .
N3 C4 H4 126.4 . .
C4 C5 N1 106.82(17) . .
C4 C5 H5 126.6 . .
N1 C5 H5 126.6 . .
N3 C6 C7 112.41(16) . .
N3 C6 H61 109.1 . .
C7 C6 H61 109.1 . .
N3 C6 H62 109.1 . .
C7 C6 H62 109.1 . .
H61 C6 H62 107.9 . .
O8 C7 C6 106.49(17) . .
O8 C7 H71 110.4 . .
C6 C7 H71 110.4 . .
O8 C7 H72 110.4 . .
C6 C7 H72 110.4 . .
H71 C7 H72 108.6 . .
C11 O8 C7 116.95(19) . .
O8 C11 C16 124.4(2) . .
O8 C11 C12 114.6(2) . .
C16 C11 C12 121.0(2) . .
C13 C12 C11 119.4(3) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
C12 C13 C14 120.0(3) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C15 C14 C13 120.1(3) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C16 120.6(3) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C11 C16 C15 118.9(3) . .
C11 C16 H16 120.5 . .
C15 C16 H16 120.5 . .
N1 C21 N1 107.8(2) . 2
N1 C21 H21 110.3 . .
N1 C21 H21 109.9 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.348(2) .
N1 C5 1.379(3) .
N1 C21 1.455(2) .
C2 N3 1.327(2) .
C2 H2 0.9500 .
N3 C4 1.378(2) .
N3 C6 1.483(2) .
C4 C5 1.348(3) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 C7 1.513(3) .
C6 H61 0.9900 .
C6 H62 0.9900 .
C7 O8 1.428(3) .
C7 H71 0.9900 .
C7 H72 0.9900 .
O8 C11 1.371(3) .
C11 C16 1.372(4) .
C11 C12 1.399(4) .
C12 C13 1.383(4) .
C12 H12 0.9500 .
C13 C14 1.393(6) .
C13 H13 0.9500 .
C14 C15 1.372(6) .
C14 H14 0.9500 .
C15 C16 1.405(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 N1 1.455(2) 2
C21 H21 0.9600 .
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
_geom_torsion_site_symmetry_4
C5 N1 C2 N3 -1.2(2) .
C21 N1 C2 N3 -171.92(17) .
N1 C2 N3 C4 1.1(2) .
N1 C2 N3 C6 176.55(17) .
C2 N3 C4 C5 -0.6(2) .
C6 N3 C4 C5 -176.18(18) .
N3 C4 C5 N1 -0.2(2) .
C2 N1 C5 C4 0.9(2) .
C21 N1 C5 C4 171.75(18) .
C2 N3 C6 C7 68.6(3) .
C4 N3 C6 C7 -116.6(2) .
N3 C6 C7 O8 -68.8(2) .
C6 C7 O8 C11 -169.90(17) .
C7 O8 C11 C16 -6.7(3) .
C7 O8 C11 C12 174.00(18) .
O8 C11 C12 C13 178.9(2) .
C16 C11 C12 C13 -0.4(4) .
C11 C12 C13 C14 0.7(4) .
C12 C13 C14 C15 -0.5(4) .
C13 C14 C15 C16 0.0(4) .
O8 C11 C16 C15 -179.3(2) .
C12 C11 C16 C15 -0.1(4) .
C14 C15 C16 C11 0.3(4) .
C2 N1 C21 N1 103.69(19) 2
C5 N1 C21 N1 -65.66(16) 2
