#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/21/7232144.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_7232144
loop_
_publ_author_name
'Wilm, Lukas F. B.'
'Eder, Tobias'
'Mück-Lichtenfeld, Christian'
'Mehlmann, Paul'
'Wünsche, Marius'
'Buß, Florenz'
'Dielmann, Fabian'
_publ_section_title
;
 Reversible CO2 fixation by N-heterocyclic imines forming water-stable
 zwitterionic nitrogen-base--CO2 adducts
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              640
_journal_paper_doi               10.1039/C8GC02952K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C8 H13 N3 O2'
_chemical_formula_sum            'C8 H13 N3 O2'
_chemical_formula_weight         183.21
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.1304(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6679(3)
_cell_length_b                   14.6889(5)
_cell_length_c                   9.6025(4)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.507
_cell_measurement_theta_min      3.442
_cell_volume                     912.05(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20261
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         3.533
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0709 before and 0.0385 after correction.
The Ratio of minimum to maximum transmission is 0.9156.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0391
_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)+(0.0589P)²+0.3913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2583
_reflns_number_total             2785
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8gc02952k2.cif
_cod_data_source_block           p21c_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7232134--7232146.cif.'
_cod_database_code               7232144
_shelxl_version_number           2013-4
_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.
;
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5A(0.021) H5B(0.021) H5C(0.021) H6A(0.027) H6B(0.027) H6C(0.027)
 H7A(0.027) H7B(0.027) H7C(0.027) H8A(0.029) H8B(0.029) H8C(0.029)
 Fixed X: H5A(0.5068) H5B(0.557) H5C(0.4444) H6A(0.1304) H6B(-0.0418)
 H6C(0.1981) H7A(-0.2911) H7B(-0.3027) H7C(-0.3793) H8A(-0.1728) H8B(-0.0065)
 H8C(-0.2052)
 Fixed Y: H5A(0.4742) H5B(0.369) H5C(0.3995) H6A(0.5211) H6B(0.5692)
 H6C(0.5825) H7A(0.4728) H7B(0.5148) H7C(0.4128) H8A(0.2396) H8B(0.2567)
 H8C(0.3211)
 Fixed Z: H5A(0.3526) H5B(0.3339) H5C(0.4558) H6A(0.4382) H6B(0.3146)
 H6C(0.3197) H7A(-0.0319) H7B(0.1197) H7C(0.079) H8A(0.0169) H8B(-0.0756) H8C(-
 0.0969)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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
O1 O 0.32050(12) 0.20245(5) 0.35557(7) 0.01803(16) Uani 1 1 d .
O2 O 0.47455(12) 0.12569(5) 0.20725(8) 0.01992(17) Uani 1 1 d .
N1 N 0.33522(13) 0.26417(5) 0.14133(8) 0.01378(16) Uani 1 1 d .
H1 H 0.350(2) 0.2580(11) 0.0578(17) 0.024(4) Uiso 1 1 d .
N2 N 0.25680(12) 0.40062(5) 0.25690(8) 0.01189(16) Uani 1 1 d .
N3 N 0.01215(12) 0.34710(5) 0.08442(8) 0.01331(16) Uani 1 1 d .
C1 C 0.38035(13) 0.19122(6) 0.24307(9) 0.01210(17) Uani 1 1 d .
C2 C 0.20773(14) 0.33365(6) 0.16003(9) 0.01207(17) Uani 1 1 d .
C3 C 0.08729(14) 0.45812(6) 0.24435(10) 0.01322(17) Uani 1 1 d .
C4 C -0.06595(14) 0.42509(6) 0.13499(10) 0.01388(18) Uani 1 1 d .
C5 C 0.45776(14) 0.41175(6) 0.35812(10) 0.01417(17) Uani 1 1 d .
H5A H 0.5068 0.4742 0.3526 0.021 Uiso 1 1 calc GR
H5B H 0.5570 0.3690 0.3339 0.021 Uiso 1 1 calc GR
H5C H 0.4444 0.3995 0.4558 0.021 Uiso 1 1 calc GR
C6 C 0.09405(15) 0.53970(6) 0.33713(11) 0.01787(19) Uani 1 1 d .
H6A H 0.1304 0.5211 0.4382 0.027 Uiso 1 1 calc GR
H6B H -0.0418 0.5692 0.3146 0.027 Uiso 1 1 calc GR
H6C H 0.1981 0.5825 0.3197 0.027 Uiso 1 1 calc GR
C7 C -0.27778(15) 0.45930(7) 0.06994(11) 0.01807(19) Uani 1 1 d .
H7A H -0.2911 0.4728 -0.0319 0.027 Uiso 1 1 calc GR
H7B H -0.3027 0.5148 0.1197 0.027 Uiso 1 1 calc GR
H7C H -0.3793 0.4128 0.0790 0.027 Uiso 1 1 calc GR
C8 C -0.10252(16) 0.28610(7) -0.02695(11) 0.0195(2) Uani 1 1 d .
H8A H -0.1728 0.2396 0.0169 0.029 Uiso 1 1 calc GR
H8B H -0.0065 0.2567 -0.0756 0.029 Uiso 1 1 calc GR
H8C H -0.2052 0.3211 -0.0969 0.029 Uiso 1 1 calc GR
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C1 120.18(8)
C2 N2 C3 109.28(7)
C2 N2 C5 125.03(8)
C3 N2 C5 125.69(7)
C2 N3 C4 109.18(7)
C2 N3 C8 124.84(8)
C4 N3 C8 125.88(8)
O1 C1 N1 115.63(8)
O2 C1 O1 129.09(9)
O2 C1 N1 115.28(8)
N2 C2 N1 125.82(8)
N2 C2 N3 107.93(8)
N3 C2 N1 126.24(8)
N2 C3 C6 122.11(8)
C4 C3 N2 106.90(8)
C4 C3 C6 130.97(9)
N3 C4 C7 121.95(8)
C3 C4 N3 106.70(8)
C3 C4 C7 131.33(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2506(11)
O2 C1 1.2430(11)
N1 C1 1.4317(11)
N1 C2 1.3679(11)
N2 C2 1.3384(11)
N2 C3 1.3925(11)
N2 C5 1.4598(11)
N3 C2 1.3433(11)
N3 C4 1.3939(12)
N3 C8 1.4602(12)
C3 C4 1.3632(13)
C3 C6 1.4872(13)
C4 C7 1.4856(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139205357
