#------------------------------------------------------------------------------
#$Date: 2020-10-03 04:22:08 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256967 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/92/1559248.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_1559248
loop_
_publ_author_name
'Maiti, Avijit'
'Chandra, Shubhadeep'
'Sarkar, Biprajit'
'Jana, Anukul'
_publ_section_title
;
 Acyclic Diaminocarbene-Based Thiele, Chichibabin, and Müller
 Hydrocarbons
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03622F
_journal_year                    2020
_chemical_formula_moiety         'C24 H44 N4'
_chemical_formula_sum            'C24 H44 N4'
_chemical_formula_weight         388.63
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-12 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.827(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8244(13)
_cell_length_b                   9.4809(18)
_cell_length_c                   11.8030(14)
_cell_measurement_reflns_used    2323
_cell_measurement_temperature    240.01(10)
_cell_measurement_theta_max      28.6390
_cell_measurement_theta_min      3.3260
_cell_volume                     1209.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  32.00   0.50  175.00    --    7.10  -3.00 149.00   50
  2  ω    -32.00  -7.00   0.50  175.00    --   -7.50   3.00 -32.00   50
  3  ω     51.00  77.00   0.50  175.00    --    7.10  77.00 150.00   52
  4  ω     50.00  95.00   0.50  175.00    --    7.10  77.00  30.00   90
  5  ω     50.00  93.00   0.50  175.00    --    7.10  77.00 -90.00   86
  6  ω     51.00  95.00   0.50  175.00    --    7.10  77.00   0.00   88
  7  ω    -96.00  22.00   0.50  175.00    --   -7.50 -57.00 -60.00  236
  8  ω    -23.00   3.00   0.50  175.00    --   -7.50 -82.00 -60.00   52
  9  ω    -52.00 -27.00   0.50  175.00    --   -7.50 -82.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0316874000
_diffrn_orient_matrix_UB_12      -0.0017478000
_diffrn_orient_matrix_UB_13      -0.0540660000
_diffrn_orient_matrix_UB_21      0.0574120000
_diffrn_orient_matrix_UB_22      -0.0021378000
_diffrn_orient_matrix_UB_23      -0.0263365000
_diffrn_orient_matrix_UB_31      -0.0008962000
_diffrn_orient_matrix_UB_32      -0.0747897000
_diffrn_orient_matrix_UB_33      0.0020307000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1273
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2045
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.757
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.1025
_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)+(0.1865P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2537
_refine_ls_wR_factor_ref         0.2803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1358
_reflns_number_total             2045
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03622f2.cif
_cod_data_source_block           aj0888
_cod_database_code               1559248
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N '
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.991
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.723(8)
 0.277(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C),
 C10(H10A,H10B,H10C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.099
_oxdiff_exptl_absorpt_empirical_full_min 0.276
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2103(2) 0.5782(3) 0.3197(2) 0.0322(8) Uani 1 1 d . . . . .
N2 N 0.3451(3) 0.4541(3) 0.2081(2) 0.0326(8) Uani 1 1 d . . . . .
C1 C 0.3243(3) 0.5127(3) 0.3140(2) 0.0293(8) Uani 1 1 d . . . . .
C5 C 0.1728(3) 0.6889(4) 0.2370(3) 0.0362(9) Uani 1 1 d . . . . .
H5 H 0.231036 0.683455 0.175039 0.043 Uiso 1 1 calc R . . . .
C9 C 0.2535(3) 0.3585(4) 0.1540(3) 0.0361(9) Uani 1 1 d . . . . .
H9 H 0.172830 0.379037 0.186367 0.043 Uiso 1 1 calc R . . . .
C4 C 0.5879(3) 0.3925(4) 0.5035(3) 0.0336(9) Uani 1 1 d . . . . .
H4 H 0.646865 0.319661 0.505551 0.040 Uiso 1 1 calc R . . . .
C2 C 0.4095(3) 0.5049(3) 0.4050(2) 0.0295(8) Uani 1 1 d . . . . .
C3 C 0.5037(3) 0.3985(4) 0.4160(2) 0.0323(9) Uani 1 1 d . . . . .
H3 H 0.506631 0.329405 0.359017 0.039 Uiso 1 1 calc R . . . .
C8 C 0.1360(4) 0.5605(5) 0.4177(3) 0.0491(11) Uani 1 1 d . . . . .
H8A H 0.169136 0.483626 0.464109 0.074 Uiso 1 1 calc GR . . . .
H8B H 0.051383 0.539285 0.392614 0.074 Uiso 1 1 calc GR . . . .
H8C H 0.137875 0.646848 0.461863 0.074 Uiso 1 1 calc GR . . . .
C12 C 0.4656(4) 0.4592(5) 0.1618(3) 0.0491(11) Uani 1 1 d . . . . .
H12A H 0.519307 0.519949 0.208439 0.074 Uiso 1 1 calc GR . . . .
H12B H 0.458324 0.496277 0.085145 0.074 Uiso 1 1 calc GR . . . .
H12C H 0.500294 0.364966 0.160578 0.074 Uiso 1 1 calc GR . . . .
C7 C 0.0454(4) 0.6661(5) 0.1837(4) 0.0601(12) Uani 1 1 d . . . . .
H7A H 0.039908 0.572040 0.151540 0.090 Uiso 1 1 calc GR . . . .
H7B H 0.029442 0.735286 0.124163 0.090 Uiso 1 1 calc GR . . . .
H7C H -0.015303 0.676381 0.240849 0.090 Uiso 1 1 calc GR . . . .
C11 C 0.2844(4) 0.2056(4) 0.1799(3) 0.0523(11) Uani 1 1 d . . . . .
H11A H 0.357570 0.178596 0.140934 0.078 Uiso 1 1 calc GR . . . .
H11B H 0.215486 0.146269 0.154468 0.078 Uiso 1 1 calc GR . . . .
H11C H 0.299881 0.194022 0.261063 0.078 Uiso 1 1 calc GR . . . .
C10 C 0.2387(5) 0.3817(6) 0.0276(3) 0.0682(14) Uani 1 1 d . . . . .
H10A H 0.229280 0.481743 0.012186 0.102 Uiso 1 1 calc GR . . . .
H10B H 0.166034 0.331738 -0.002326 0.102 Uiso 1 1 calc GR . . . .
H10C H 0.311316 0.346643 -0.008336 0.102 Uiso 1 1 calc GR . . . .
C6 C 0.1852(5) 0.8340(5) 0.2863(4) 0.0681(14) Uani 1 1 d . . . . .
H6A H 0.126360 0.845698 0.345020 0.102 Uiso 1 1 calc GR . . . .
H6B H 0.168747 0.903423 0.227133 0.102 Uiso 1 1 calc GR . . . .
H6C H 0.268483 0.846925 0.318852 0.102 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'
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
C1 N1 C5 120.1(3) . . ?
C1 N1 C8 121.1(3) . . ?
C8 N1 C5 117.7(3) . . ?
C1 N2 C9 120.1(3) . . ?
C1 N2 C12 121.1(3) . . ?
C12 N2 C9 117.4(3) . . ?
N1 C1 N2 113.9(3) . . ?
C2 C1 N1 123.2(3) . . ?
C2 C1 N2 122.9(3) . . ?
N1 C5 H5 106.7 . . ?
N1 C5 C7 113.0(3) . . ?
N1 C5 C6 112.3(3) . . ?
C7 C5 H5 106.7 . . ?
C6 C5 H5 106.7 . . ?
C6 C5 C7 110.9(3) . . ?
N2 C9 H9 107.5 . . ?
N2 C9 C11 111.5(3) . . ?
N2 C9 C10 112.2(3) . . ?
C11 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C10 C9 C11 110.6(3) . . ?
C2 C4 H4 119.0 3_666 . ?
C3 C4 H4 119.0 . . ?
C3 C4 C2 122.0(3) . 3_666 ?
C1 C2 C4 122.0(3) . 3_666 ?
C1 C2 C3 123.4(3) . . ?
C3 C2 C4 114.6(3) . 3_666 ?
C4 C3 C2 123.4(3) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
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
N1 C1 1.386(4) . ?
N1 C5 1.477(4) . ?
N1 C8 1.450(4) . ?
N2 C1 1.396(4) . ?
N2 C9 1.467(4) . ?
N2 C12 1.440(4) . ?
C1 C2 1.383(4) . ?
C5 H5 0.9900 . ?
C5 C7 1.503(5) . ?
C5 C6 1.497(6) . ?
C9 H9 0.9900 . ?
C9 C11 1.515(6) . ?
C9 C10 1.509(5) . ?
C4 H4 0.9400 . ?
C4 C2 1.453(5) 3_666 ?
C4 C3 1.345(5) . ?
C2 C3 1.436(5) . ?
C3 H3 0.9400 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.723(8)
2 0.277(8)
