#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:19:08 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289576 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/28/7062882.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_7062882
loop_
_publ_author_name
'Mesías-Salazar, Ángela'
'Rojas, René S.'
'Carrillo-Hermosilla, Fernando'
'Martínez, Javier'
'Antiñolo, Antonio'
'Trofymchuk, Oleksandra S.'
'Nachtigall, Fabiane M.'
'Santos, Leonardo S.'
'Daniliuc, Constantin G.'
_publ_section_title
;
 Guanidinium iodide salts as single component catalysts for CO2 to epoxide
 fixation
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              105
_journal_page_last               111
_journal_paper_doi               10.1039/D3NJ03959E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_sum            'C36 H60 I2 N6 O2'
_chemical_formula_weight         862.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2023-06-05 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.8630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8424(2)
_cell_length_b                   14.7304(3)
_cell_length_c                   12.1460(2)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6212
_cell_measurement_theta_min      4.0820
_cell_volume                     1937.66(6)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25772
_diffrn_reflns_theta_full        66.63
_diffrn_reflns_theta_max         66.63
_diffrn_reflns_theta_min         4.08
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    13.039
_exptl_absorpt_correction_T_max  0.42
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.608
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0224
_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)+(0.0259P)²+1.7290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0542
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                3279
_reflns_number_total             3425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj03959e2.cif
_cod_data_source_block           dan9751_1j
_cod_depositor_comments
'Adding full bibliography for 7062881--7062882.cif.'
_cod_database_code               7062882
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.38725(2) 0.47006(2) 0.14152(2) 0.01946(7) Uani d . . . 1 . .
N N1 0.76015(17) 0.58821(13) 0.31969(16) 0.0111(4) Uani d . . . 1 . .
H H1 0.735(3) 0.550(2) 0.269(3) 0.014(7) Uiso d . . . 1 . .
N N2 0.75183(17) 0.74133(13) 0.36871(16) 0.0106(4) Uani d . . . 1 . .
H H2 0.708(2) 0.7838(19) 0.362(2) 0.008(6) Uiso d . . . 1 . .
N N3 0.58923(17) 0.67333(13) 0.21229(16) 0.0114(4) Uani d . . . 1 . .
H H3 0.555(3) 0.624(2) 0.185(2) 0.016(7) Uiso d . . . 1 . .
O O1 0.68868(19) 0.44650(13) 0.15310(17) 0.0246(4) Uani d . . . 1 . .
H H1A 0.624(4) 0.436(3) 0.149(3) 0.039(11) Uiso d . . . 1 . .
H H2A 0.677(4) 0.463(3) 0.081(5) 0.064(14) Uiso d . . . 1 . .
C C1 0.7013(2) 0.66885(14) 0.30147(18) 0.0092(4) Uani d . . . 1 . .
C C11 0.8439(2) 0.55407(14) 0.43410(18) 0.0095(4) Uani d . . . 1 . .
C C12 0.8119(2) 0.55335(14) 0.53052(19) 0.0117(4) Uani d . . . 1 . .
H H12 0.7343 0.577 0.5223 0.014 Uiso calc U . R 1 . .
C C13 0.8939(2) 0.51760(15) 0.64193(18) 0.0126(5) Uani d . . . 1 . .
H H13 0.871 0.5174 0.7084 0.015 Uiso calc U . R 1 . .
C C14 1.0057(2) 0.48325(14) 0.65532(18) 0.0111(4) Uani d . . . 1 . .
H H14 1.0602 0.4599 0.7311 0.013 Uiso calc U . R 1 . .
C C15 1.0413(2) 0.48219(13) 0.55673(18) 0.0090(4) Uani d . . . 1 . .
C C21 0.88430(19) 0.75808(14) 0.44109(18) 0.0099(4) Uani d . . . 1 . .
H H21 0.9317 0.7022 0.4398 0.012 Uiso calc U . R 1 . .
C C22 0.9288(2) 0.83658(15) 0.38630(18) 0.0121(4) Uani d . . . 1 . .
H H22A 0.9175 0.8205 0.3033 0.014 Uiso calc U . R 1 . .
H H22B 0.8788 0.8913 0.3821 0.014 Uiso calc U . R 1 . .
C C23 1.0650(2) 0.85715(16) 0.4618(2) 0.0176(5) Uani d . . . 1 . .
H H23A 1.1158 0.8047 0.4584 0.021 Uiso calc U . R 1 . .
H H23B 1.0904 0.9105 0.4277 0.021 Uiso calc U . R 1 . .
C C24 1.0882(2) 0.87639(16) 0.5926(2) 0.0182(5) Uani d . . . 1 . .
H H24A 1.045 0.9329 0.5969 0.022 Uiso calc U . R 1 . .
H H24B 1.1778 0.8855 0.6401 0.022 Uiso calc U . R 1 . .
C C25 1.0428(2) 0.79814(16) 0.64672(19) 0.0175(5) Uani d . . . 1 . .
H H25A 1.0917 0.7429 0.6499 0.021 Uiso calc U . R 1 . .
H H25B 1.0549 0.8138 0.73 0.021 Uiso calc U . R 1 . .
C C26 0.9063(2) 0.77913(15) 0.57151(18) 0.0132(4) Uani d . . . 1 . .
H H26A 0.8567 0.8327 0.5736 0.016 Uiso calc U . R 1 . .
H H26B 0.8793 0.7269 0.6062 0.016 Uiso calc U . R 1 . .
C C31 0.5272(2) 0.75590(14) 0.14706(18) 0.0109(4) Uani d . . . 1 . .
H H31 0.5633 0.8094 0.2005 0.013 Uiso calc U . R 1 . .
C C32 0.5512(2) 0.76745(18) 0.0342(2) 0.0220(5) Uani d . . . 1 . .
H H32A 0.5212 0.7133 -0.0177 0.026 Uiso calc U . R 1 . .
H H32B 0.6411 0.7731 0.0565 0.026 Uiso calc U . R 1 . .
C C33 0.4849(3) 0.85240(19) -0.0352(2) 0.0276(6) Uani d . . . 1 . .
H H33A 0.5202 0.9071 0.0143 0.033 Uiso calc U . R 1 . .
H H33B 0.4982 0.8577 -0.1103 0.033 Uiso calc U . R 1 . .
C C34 0.3480(2) 0.84755(18) -0.0656(2) 0.0228(5) Uani d . . . 1 . .
H H34A 0.3116 0.7955 -0.1199 0.027 Uiso calc U . R 1 . .
H H34B 0.3074 0.9036 -0.1082 0.027 Uiso calc U . R 1 . .
C C35 0.3247(2) 0.83677(17) 0.0476(2) 0.0208(5) Uani d . . . 1 . .
H H35A 0.2349 0.8315 0.0256 0.025 Uiso calc U . R 1 . .
H H35B 0.355 0.8913 0.0988 0.025 Uiso calc U . R 1 . .
C C36 0.3902(2) 0.75245(18) 0.1186(2) 0.0239(6) Uani d . . . 1 . .
H H36A 0.3781 0.749 0.1945 0.029 Uiso calc U . R 1 . .
H H36B 0.3537 0.6973 0.0708 0.029 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C1 N1 C11 . . 125.24(18) ?
C1 N1 H1 . . 119.(2) ?
C11 N1 H1 . . 113.(2) ?
C1 N2 C21 . . 127.25(19) ?
C1 N2 H2 . . 117.0(18) ?
C21 N2 H2 . . 115.1(18) ?
C1 N3 C31 . . 126.37(18) ?
C1 N3 H3 . . 116.5(19) ?
C31 N3 H3 . . 116.7(19) ?
H1A O1 H2A . . 104.(4) ?
N2 C1 N3 . . 120.78(19) ?
N2 C1 N1 . . 122.1(2) ?
N3 C1 N1 . . 117.08(19) ?
C12 C11 C15 . 3_766 121.10(19) ?
C12 C11 N1 . . 120.7(2) ?
C15 C11 N1 3_766 . 118.18(18) ?
C11 C12 C13 . . 120.2(2) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C14 C13 C12 . . 120.72(19) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 120.54(19) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C14 C15 C11 . 3_766 122.55(19) ?
C14 C15 C15 . 3_766 119.2(2) ?
C11 C15 C15 3_766 3_766 118.3(2) ?
N2 C21 C26 . . 110.20(17) ?
N2 C21 C22 . . 109.73(17) ?
C26 C21 C22 . . 110.67(17) ?
N2 C21 H21 . . 108.7 ?
C26 C21 H21 . . 108.7 ?
C22 C21 H21 . . 108.7 ?
C23 C22 C21 . . 110.75(17) ?
C23 C22 H22A . . 109.5 ?
C21 C22 H22A . . 109.5 ?
C23 C22 H22B . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
C24 C23 C22 . . 111.36(18) ?
C24 C23 H23A . . 109.4 ?
C22 C23 H23A . . 109.4 ?
C24 C23 H23B . . 109.4 ?
C22 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
C23 C24 C25 . . 111.18(19) ?
C23 C24 H24A . . 109.4 ?
C25 C24 H24A . . 109.4 ?
C23 C24 H24B . . 109.4 ?
C25 C24 H24B . . 109.4 ?
H24A C24 H24B . . 108.0 ?
C26 C25 C24 . . 110.65(18) ?
C26 C25 H25A . . 109.5 ?
C24 C25 H25A . . 109.5 ?
C26 C25 H25B . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 108.1 ?
C25 C26 C21 . . 110.61(18) ?
C25 C26 H26A . . 109.5 ?
C21 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
C21 C26 H26B . . 109.5 ?
H26A C26 H26B . . 108.1 ?
N3 C31 C36 . . 110.42(18) ?
N3 C31 C32 . . 110.08(17) ?
C36 C31 C32 . . 111.80(19) ?
N3 C31 H31 . . 108.1 ?
C36 C31 H31 . . 108.1 ?
C32 C31 H31 . . 108.1 ?
C31 C32 C33 . . 110.27(19) ?
C31 C32 H32A . . 109.6 ?
C33 C32 H32A . . 109.6 ?
C31 C32 H32B . . 109.6 ?
C33 C32 H32B . . 109.6 ?
H32A C32 H32B . . 108.1 ?
C34 C33 C32 . . 110.8(2) ?
C34 C33 H33A . . 109.5 ?
C32 C33 H33A . . 109.5 ?
C34 C33 H33B . . 109.5 ?
C32 C33 H33B . . 109.5 ?
H33A C33 H33B . . 108.1 ?
C33 C34 C35 . . 110.7(2) ?
C33 C34 H34A . . 109.5 ?
C35 C34 H34A . . 109.5 ?
C33 C34 H34B . . 109.5 ?
C35 C34 H34B . . 109.5 ?
H34A C34 H34B . . 108.1 ?
C34 C35 C36 . . 111.0(2) ?
C34 C35 H35A . . 109.4 ?
C36 C35 H35A . . 109.4 ?
C34 C35 H35B . . 109.4 ?
C36 C35 H35B . . 109.4 ?
H35A C35 H35B . . 108.0 ?
C31 C36 C35 . . 110.63(19) ?
C31 C36 H36A . . 109.5 ?
C35 C36 H36A . . 109.5 ?
C31 C36 H36B . . 109.5 ?
C35 C36 H36B . . 109.5 ?
H36A C36 H36B . . 108.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.349(3) ?
N1 C11 . 1.433(3) ?
N1 H1 . 0.80(3) ?
N2 C1 . 1.330(3) ?
N2 C21 . 1.476(3) ?
N2 H2 . 0.80(3) ?
N3 C1 . 1.333(3) ?
N3 C31 . 1.475(3) ?
N3 H3 . 0.83(3) ?
O1 H1A . 0.77(4) ?
O1 H2A . 0.86(5) ?
C11 C12 . 1.369(3) ?
C11 C15 3_766 1.422(3) ?
C12 C13 . 1.410(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.365(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.422(3) ?
C14 H14 . 0.95 ?
C15 C11 3_766 1.422(3) ?
C15 C15 3_766 1.429(4) ?
C21 C26 . 1.530(3) ?
C21 C22 . 1.530(3) ?
C21 H21 . 1.0 ?
C22 C23 . 1.528(3) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 C24 . 1.524(3) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.529(3) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 C26 . 1.527(3) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C31 C36 . 1.517(3) ?
C31 C32 . 1.518(3) ?
C31 H31 . 1.0 ?
C32 C33 . 1.535(3) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 C34 . 1.512(4) ?
C33 H33A . 0.99 ?
C33 H33B . 0.99 ?
C34 C35 . 1.516(3) ?
C34 H34A . 0.99 ?
C34 H34B . 0.99 ?
C35 C36 . 1.531(3) ?
C35 H35A . 0.99 ?
C35 H35B . 0.99 ?
C36 H36A . 0.99 ?
C36 H36B . 0.99 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . 0.80(3) 2.00(3) 2.790(3) 174.(3) ?
N2 H2 I1 2_655 0.80(3) 2.96(3) 3.7302(19) 163.(2) ?
N3 H3 I1 . 0.83(3) 2.92(3) 3.7097(19) 160.(2) ?
O1 H1A I1 . 0.77(4) 2.81(4) 3.532(2) 158.(4) ?
O1 H2A I1 3_665 0.86(5) 2.69(5) 3.538(2) 172.(4) ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 N2 C1 N3 . . . . -158.24(19) ?
C21 N2 C1 N1 . . . . 21.7(3) ?
C31 N3 C1 N2 . . . . 23.8(3) ?
C31 N3 C1 N1 . . . . -156.19(19) ?
C11 N1 C1 N2 . . . . 32.5(3) ?
C11 N1 C1 N3 . . . . -147.6(2) ?
C1 N1 C11 C12 . . . . 50.1(3) ?
C1 N1 C11 C15 . . . 3_766 -132.3(2) ?
C15 C11 C12 C13 3_766 . . . 1.0(3) ?
N1 C11 C12 C13 . . . . 178.48(19) ?
C11 C12 C13 C14 . . . . -0.1(3) ?
C12 C13 C14 C15 . . . . -0.5(3) ?
C13 C14 C15 C11 . . . 3_766 -179.1(2) ?
C13 C14 C15 C15 . . . 3_766 0.2(4) ?
C1 N2 C21 C26 . . . . -125.7(2) ?
C1 N2 C21 C22 . . . . 112.2(2) ?
N2 C21 C22 C23 . . . . 178.32(17) ?
C26 C21 C22 C23 . . . . 56.5(2) ?
C21 C22 C23 C24 . . . . -55.5(2) ?
C22 C23 C24 C25 . . . . 55.5(3) ?
C23 C24 C25 C26 . . . . -56.1(3) ?
C24 C25 C26 C21 . . . . 57.2(2) ?
N2 C21 C26 C25 . . . . -179.05(18) ?
C22 C21 C26 C25 . . . . -57.5(2) ?
C1 N3 C31 C36 . . . . -142.5(2) ?
C1 N3 C31 C32 . . . . 93.6(2) ?
N3 C31 C32 C33 . . . . 179.0(2) ?
C36 C31 C32 C33 . . . . 55.9(3) ?
C31 C32 C33 C34 . . . . -56.7(3) ?
C32 C33 C34 C35 . . . . 57.6(3) ?
C33 C34 C35 C36 . . . . -57.1(3) ?
N3 C31 C36 C35 . . . . -178.36(19) ?
C32 C31 C36 C35 . . . . -55.4(3) ?
C34 C35 C36 C31 . . . . 55.6(3) ?
