#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/83/7028375.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_7028375
loop_
_publ_author_name
'Theuergarten, Eileen'
'Bannenberg, Thomas'
'Walter, Marc D.'
'Holschumacher, Dirk'
'Freytag, Matthias'
'Daniliuc, Constantin G.'
'Jones, Peter G.'
'Tamm, Matthias'
_publ_section_title
;
 Computational and experimental investigations of CO2 and N2O fixation by
 sterically demanding N-heterocyclic carbenes (NHC) and NHC/borane FLP
 systems.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1651
_journal_page_last               1662
_journal_paper_doi               10.1039/c3dt52742e
_journal_volume                  43
_journal_year                    2014
_chemical_formula_sum            'C11 H20 N4 O'
_chemical_formula_weight         224.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.208(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2956(2)
_cell_length_b                   11.7049(2)
_cell_length_c                   11.2144(2)
_cell_measurement_reflns_used    14116
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7649
_cell_measurement_theta_min      3.7733
_cell_volume                     1204.45(4)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) 
(compiled Aug  3 2011,13:03:54) 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) 
(compiled Aug  3 2011,13:03:54) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) 
(compiled Aug  3 2011,13:03:54) 
;
_computing_molecular_graphics    'BRUKER XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0098
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19755
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         75.95
_diffrn_reflns_theta_min         5.50
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) 
(compiled Aug  3 2011,13:03:54)  
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0491P)²+0.3782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                2365
_reflns_number_total             2504
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52742e.txt
_cod_data_source_block           temp_eileen35
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7028375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09593(8) 0.45566(7) 0.31169(7) 0.01814(19) Uani 1 1 d . . .
N2 N -0.10075(8) 0.50197(7) 0.18486(7) 0.01809(19) Uani 1 1 d . . .
N3 N 0.06092(10) 0.65649(7) 0.27635(8) 0.0251(2) Uani 1 1 d D . .
N4 N -0.04233(13) 0.71486(9) 0.32030(11) 0.0251(3) Uani 0.902(3) 1 d PDU A 1
O O -0.01179(10) 0.81880(7) 0.33767(9) 0.0348(3) Uani 0.902(3) 1 d PD A 1
N4' N 0.0297(14) 0.7461(10) 0.3141(10) 0.037(3) Uiso 0.098(3) 1 d PDU A 2
O' O -0.0766(11) 0.7124(9) 0.3700(10) 0.035(3) Uiso 0.098(3) 1 d PDU A 2
C1 C 0.01769(10) 0.54492(8) 0.25812(8) 0.0176(2) Uani 1 1 d . A .
C2 C 0.02221(12) 0.35595(9) 0.27501(9) 0.0241(2) Uani 1 1 d . . .
H2 H 0.0520 0.2808 0.2996 0.029 Uiso 1 1 calc R . .
C3 C -0.09923(11) 0.38421(9) 0.19837(9) 0.0236(2) Uani 1 1 d . . .
H3 H -0.1711 0.3326 0.1603 0.028 Uiso 1 1 calc R . .
C4 C 0.23531(10) 0.46378(9) 0.40098(9) 0.0197(2) Uani 1 1 d . . .
C5 C 0.20553(11) 0.52921(9) 0.51226(9) 0.0230(2) Uani 1 1 d . . .
H5A H 0.1677 0.6053 0.4880 0.034 Uiso 1 1 calc R . .
H5B H 0.2962 0.5367 0.5698 0.034 Uiso 1 1 calc R . .
H5C H 0.1335 0.4876 0.5504 0.034 Uiso 1 1 calc R . .
C6 C 0.35015(11) 0.52248(11) 0.33943(10) 0.0283(3) Uani 1 1 d . . .
H6A H 0.3687 0.4764 0.2705 0.043 Uiso 1 1 calc R . .
H6B H 0.4406 0.5306 0.3971 0.043 Uiso 1 1 calc R . .
H6C H 0.3150 0.5982 0.3111 0.043 Uiso 1 1 calc R . .
C7 C 0.28506(12) 0.34267(10) 0.43809(10) 0.0298(3) Uani 1 1 d . . .
H7A H 0.2112 0.3054 0.4780 0.045 Uiso 1 1 calc R . .
H7B H 0.3776 0.3460 0.4939 0.045 Uiso 1 1 calc R . .
H7C H 0.2983 0.2989 0.3661 0.045 Uiso 1 1 calc R . .
C8 C -0.21489(10) 0.56433(9) 0.09730(9) 0.0204(2) Uani 1 1 d . . .
C9 C -0.14721(12) 0.66507(11) 0.04032(11) 0.0337(3) Uani 1 1 d . . .
H9A H -0.1218 0.7251 0.1010 0.051 Uiso 1 1 calc R . .
H9B H -0.2172 0.6952 -0.0270 0.051 Uiso 1 1 calc R . .
H9C H -0.0591 0.6397 0.0103 0.051 Uiso 1 1 calc R . .
C10 C -0.33748(11) 0.60123(10) 0.16404(10) 0.0266(2) Uani 1 1 d . . .
H10A H -0.3801 0.5337 0.1966 0.040 Uiso 1 1 calc R . .
H10B H -0.4127 0.6411 0.1080 0.040 Uiso 1 1 calc R . .
H10C H -0.2986 0.6526 0.2304 0.040 Uiso 1 1 calc R . .
C11 C -0.27641(12) 0.48103(11) -0.00300(10) 0.0300(3) Uani 1 1 d . . .
H11A H -0.1967 0.4505 -0.0411 0.045 Uiso 1 1 calc R . .
H11B H -0.3460 0.5211 -0.0637 0.045 Uiso 1 1 calc R . .
H11C H -0.3260 0.4181 0.0314 0.045 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 0.0181 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'
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
C1 N1 C2 108.26(8)
C1 N1 C4 126.01(8)
C2 N1 C4 125.66(8)
C1 N2 C3 107.95(8)
C1 N2 C8 129.01(8)
C3 N2 C8 122.98(8)
N4' N3 N4 35.2(6)
N4' N3 C1 144.4(6)
N4 N3 C1 109.35(9)
O N4 N3 113.24(12)
N3 N4' O' 98.7(10)
N1 C1 N2 107.91(8)
N1 C1 N3 122.92(9)
N2 C1 N3 129.14(9)
C3 C2 N1 107.92(9)
C2 C3 N2 107.88(9)
N1 C4 C6 108.49(8)
N1 C4 C5 108.99(8)
C6 C4 C5 112.07(9)
N1 C4 C7 108.22(8)
C6 C4 C7 109.76(9)
C5 C4 C7 109.23(8)
N2 C8 C10 108.67(8)
N2 C8 C9 110.59(8)
C10 C8 C9 112.22(9)
N2 C8 C11 108.10(8)
C10 C8 C11 108.75(8)
C9 C8 C11 108.41(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3571(12)
N1 C2 1.3823(13)
N1 C4 1.5084(12)
N2 C1 1.3603(12)
N2 C3 1.3864(13)
N2 C8 1.5130(12)
N3 N4' 1.185(11)
N3 N4 1.3350(15)
N3 C1 1.3720(13)
N4 O 1.2574(14)
N4' O' 1.312(13)
C2 C3 1.3461(14)
C4 C6 1.5244(14)
C4 C5 1.5268(14)
C4 C7 1.5280(14)
C8 C10 1.5226(13)
C8 C9 1.5243(15)
C8 C11 1.5287(14)
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
N4' N3 N4 O 5.3(10)
C1 N3 N4 O -178.89(10)
N4 N3 N4' O' 18.8(6)
C1 N3 N4' O' 11.9(15)
C2 N1 C1 N2 -2.38(11)
C4 N1 C1 N2 -179.45(8)
C2 N1 C1 N3 179.66(9)
C4 N1 C1 N3 2.58(15)
C3 N2 C1 N1 3.05(10)
C8 N2 C1 N1 -174.22(8)
C3 N2 C1 N3 -179.15(10)
C8 N2 C1 N3 3.57(16)
N4' N3 C1 N1 -117.6(10)
N4 N3 C1 N1 -121.73(10)
N4' N3 C1 N2 64.9(10)
N4 N3 C1 N2 60.77(13)
C1 N1 C2 C3 0.77(12)
C4 N1 C2 C3 177.86(9)
N1 C2 C3 N2 1.11(12)
C1 N2 C3 C2 -2.58(11)
C8 N2 C3 C2 174.89(9)
C1 N1 C4 C6 -61.21(12)
C2 N1 C4 C6 122.21(10)
C1 N1 C4 C5 61.06(12)
C2 N1 C4 C5 -115.52(10)
C1 N1 C4 C7 179.75(9)
C2 N1 C4 C7 3.17(13)
C1 N2 C8 C10 -89.52(11)
C3 N2 C8 C10 93.57(11)
C1 N2 C8 C9 34.07(13)
C3 N2 C8 C9 -142.83(10)
C1 N2 C8 C11 152.62(10)
C3 N2 C8 C11 -24.29(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168348114
