#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:12:44 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255952 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126798.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_7126798
loop_
_publ_author_name
'Appel, Sebastian'
'Brüggemann, Peter'
'Ganter, Christian'
_publ_section_title
;
 A tropylium annulated N-heterocyclic carbene.
;
_journal_issue                   63
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9020
_journal_page_last               9023
_journal_paper_doi               10.1039/d0cc04482b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C6 H6 N2 O2'
_chemical_formula_weight         138.13
_chemical_name_systematic        1-methyl-1H-imidazole-4,5-dicarbaldehyde
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8712(16)
_cell_length_b                   6.840(3)
_cell_length_c                   23.770(9)
_cell_measurement_reflns_used    1648
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.195
_cell_measurement_theta_min      3.099
_cell_volume                     629.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         1.713
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0416
_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)+(0.0529P)²+0.0751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1405
_reflns_number_total             1563
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04482b2.cif
_cod_data_source_block           mo_scan_0m
_cod_depositor_comments
'Adding full bibliography for 7126798--7126803.cif.'
_cod_database_code               7126798
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4397(6) 0.0308(3) 0.15393(8) 0.0561(5) Uani 1 1 d . . . . .
C1 C 0.9442(6) 0.6195(3) 0.17219(9) 0.0394(5) Uani 1 1 d . . . . .
H1 H 1.0504 0.7294 0.1874 0.047 Uiso 1 1 calc R U . . .
N1 N 0.8540(5) 0.6041(2) 0.11775(7) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.5483(6) 0.4393(2) 0.01540(6) 0.0534(5) Uani 1 1 d . . . . .
C2 C 0.9147(7) 0.7545(3) 0.07469(10) 0.0422(5) Uani 1 1 d . . . . .
H2A H 1.0396 0.6983 0.0438 0.063 Uiso 1 1 calc R U . . .
H2B H 1.0469 0.8594 0.0906 0.063 Uiso 1 1 calc R U . . .
H2C H 0.6971 0.8039 0.0615 0.063 Uiso 1 1 calc R U . . .
N2 N 0.8663(5) 0.4622(3) 0.20181(8) 0.0411(5) Uani 1 1 d . . . . .
C3 C 0.7052(5) 0.4221(3) 0.11115(8) 0.0309(4) Uani 1 1 d . . . . .
C4 C 0.7144(5) 0.3381(3) 0.16432(8) 0.0323(4) Uani 1 1 d . . . . .
C6 C 0.5652(6) 0.3474(3) 0.05859(8) 0.0389(5) Uani 1 1 d . . . . .
H6 H 0.4830 0.2197 0.0583 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5857(7) 0.1477(3) 0.18296(9) 0.0423(5) Uani 1 1 d . . . . .
H5 H 0.6202 0.1147 0.2205 0.051 Uiso 1 1 calc 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'
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
_geom_angle_publ_flag
N2 C1 N1 112.96(19) . . ?
N2 C1 H1 123.5 . . ?
N1 C1 H1 123.5 . . ?
C1 N1 C3 106.75(16) . . ?
C1 N1 C2 125.04(18) . . ?
C3 N1 C2 128.19(17) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N2 C4 104.90(18) . . ?
N1 C3 C4 105.01(17) . . ?
N1 C3 C6 124.75(18) . . ?
C4 C3 C6 130.2(2) . . ?
N2 C4 C3 110.37(18) . . ?
N2 C4 C5 120.18(18) . . ?
C3 C4 C5 129.44(19) . . ?
O2 C6 C3 124.6(2) . . ?
O2 C6 H6 117.7 . . ?
C3 C6 H6 117.7 . . ?
O1 C5 C4 125.5(2) . . ?
O1 C5 H5 117.3 . . ?
C4 C5 H5 117.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.198(3) . ?
C1 N2 1.321(3) . ?
C1 N1 1.344(3) . ?
C1 H1 0.9300 . ?
N1 C3 1.381(3) . ?
N1 C2 1.470(3) . ?
O2 C6 1.206(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N2 C4 1.364(3) . ?
C3 C4 1.389(3) . ?
C3 C6 1.454(3) . ?
C4 C5 1.463(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C3 0.0(3) . . . . ?
N2 C1 N1 C2 -178.8(2) . . . . ?
N1 C1 N2 C4 -0.4(3) . . . . ?
C1 N1 C3 C4 0.5(2) . . . . ?
C2 N1 C3 C4 179.1(2) . . . . ?
C1 N1 C3 C6 178.8(2) . . . . ?
C2 N1 C3 C6 -2.5(3) . . . . ?
C1 N2 C4 C3 0.7(3) . . . . ?
C1 N2 C4 C5 -178.6(2) . . . . ?
N1 C3 C4 N2 -0.7(2) . . . . ?
C6 C3 C4 N2 -179.0(2) . . . . ?
N1 C3 C4 C5 178.5(2) . . . . ?
C6 C3 C4 C5 0.2(4) . . . . ?
N1 C3 C6 O2 -3.7(4) . . . . ?
C4 C3 C6 O2 174.3(2) . . . . ?
N2 C4 C5 O1 177.7(2) . . . . ?
C3 C4 C5 O1 -1.5(4) . . . . ?
