#------------------------------------------------------------------------------
#$Date: 2020-10-03 04:22:08 +0300 (Sat, 03 Oct 2020) $
#$Revision: 256967 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/92/1559247.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_1559247
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         'C28 H42 N4'
_chemical_formula_sum            'C28 H42 N4'
_chemical_formula_weight         434.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-17 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                96.010(6)
_cell_angle_beta                 105.100(6)
_cell_angle_gamma                104.691(5)
_cell_formula_units_Z            1
_cell_length_a                   8.4471(5)
_cell_length_b                   8.8406(6)
_cell_length_c                   10.0062(7)
_cell_measurement_reflns_used    4211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6590
_cell_measurement_theta_min      2.9280
_cell_volume                     686.09(9)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  39.00   0.50   11.25    --    7.20  49.00  19.00   52
  2  ω    -31.00  40.00   0.50   11.25    --    7.20 -49.00-128.00  142
  3  ω     -4.00  22.00   0.50   11.25    --   -7.60  49.00  19.00   52
  4  ω    -60.00 -35.00   0.50   11.25    --   -7.60 -49.00-128.00   50
  5  ω    -33.00  97.00   0.50   11.25    --    7.20  38.00-120.00  260
  6  ω     16.00  94.00   0.50   11.25    --    7.20 -19.00  90.00  156
  7  ω    -77.00 -18.00   0.50   11.25    --    7.20 -19.00  90.00  118
  8  ω    -76.00  22.00   0.50   11.25    --   -7.60 -77.00   0.00  196
  9  ω    -43.00  29.00   0.50   11.25    --   -7.60 -82.00  90.00  144
;
_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      0.0777253000
_diffrn_orient_matrix_UB_12      0.0627878000
_diffrn_orient_matrix_UB_13      0.0264915000
_diffrn_orient_matrix_UB_21      0.0403175000
_diffrn_orient_matrix_UB_22      -0.0435298000
_diffrn_orient_matrix_UB_23      -0.0369556000
_diffrn_orient_matrix_UB_31      -0.0246065000
_diffrn_orient_matrix_UB_32      0.0357845000
_diffrn_orient_matrix_UB_33      -0.0592420000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11405
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.013
_diffrn_reflns_theta_min         2.842
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93305
_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    1.052
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0723
_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)+(0.1222P)²+0.0969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2174
_refine_ls_wR_factor_ref         0.2363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2213
_reflns_number_total             3151
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03622f2.cif
_cod_data_source_block           aj1043
_cod_original_cell_volume        686.09(8)
_cod_database_code               1559247
_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   0.991
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C10(H10A,H10B,
 H10C), C9(H9A,H9B,H9C)
;
_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.598
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N2 N 0.7681(2) 0.41881(18) 0.70420(17) 0.0637(5) Uani 1 1 d . . . . .
N1 N 0.6399(2) 0.57488(18) 0.81093(18) 0.0646(5) Uani 1 1 d . . . . .
C5 C 0.96111(18) 0.93555(17) 0.53410(15) 0.0452(4) Uani 1 1 d . . . . .
C2 C 0.8144(2) 0.69126(19) 0.66434(17) 0.0503(4) Uani 1 1 d . . . . .
C1 C 0.7355(2) 0.56200(19) 0.73334(17) 0.0512(4) Uani 1 1 d . . . . .
C7 C 0.7396(2) 0.6974(2) 0.52602(19) 0.0649(5) Uani 1 1 d . . . . .
H7 H 0.638802 0.619542 0.474376 0.078 Uiso 1 1 calc R . . . .
C6 C 0.8115(2) 0.8169(2) 0.46261(19) 0.0641(5) Uani 1 1 d . . . . .
H6 H 0.757606 0.817635 0.369009 0.077 Uiso 1 1 calc R . . . .
C8 C 0.5942(3) 0.7213(2) 0.8365(2) 0.0731(6) Uani 1 1 d . . . . .
H8 H 0.651497 0.800938 0.789922 0.088 Uiso 1 1 calc R . . . .
C4 C 1.0345(3) 0.9282(3) 0.6725(2) 0.0813(7) Uani 1 1 d . . . . .
H4 H 1.135813 1.005412 0.724203 0.098 Uiso 1 1 calc R . . . .
C12 C 0.6923(3) 0.2855(2) 0.7663(2) 0.0712(6) Uani 1 1 d . . . . .
H12 H 0.590882 0.305423 0.785898 0.085 Uiso 1 1 calc R . . . .
C3 C 0.9621(3) 0.8096(3) 0.7367(2) 0.0823(7) Uani 1 1 d . . . . .
H3 H 1.014554 0.809875 0.830813 0.099 Uiso 1 1 calc R . . . .
C11 C 0.9066(3) 0.4054(3) 0.6495(3) 0.0900(8) Uani 1 1 d . . . . .
H11A H 0.949546 0.501088 0.616505 0.135 Uiso 1 1 calc GR . . . .
H11B H 0.865696 0.316545 0.572883 0.135 Uiso 1 1 calc GR . . . .
H11C H 0.996947 0.389489 0.722536 0.135 Uiso 1 1 calc GR . . . .
C14 C 0.6306(4) 0.1298(3) 0.6627(4) 0.1065(9) Uani 1 1 d . . . . .
H14A H 0.561972 0.142652 0.574089 0.160 Uiso 1 1 calc GR . . . .
H14B H 0.563146 0.048794 0.698696 0.160 Uiso 1 1 calc GR . . . .
H14C H 0.727638 0.099344 0.649642 0.160 Uiso 1 1 calc GR . . . .
C13 C 0.8100(4) 0.2777(4) 0.9030(3) 0.1146(11) Uani 1 1 d . . . . .
H13A H 0.910857 0.256965 0.887943 0.172 Uiso 1 1 calc GR . . . .
H13B H 0.753174 0.193859 0.942946 0.172 Uiso 1 1 calc GR . . . .
H13C H 0.842084 0.377197 0.966274 0.172 Uiso 1 1 calc GR . . . .
C10 C 0.4046(4) 0.6881(4) 0.7799(4) 0.1278(12) Uani 1 1 d . . . . .
H10A H 0.370009 0.658184 0.679219 0.192 Uiso 1 1 calc GR . . . .
H10B H 0.373324 0.781808 0.805011 0.192 Uiso 1 1 calc GR . . . .
H10C H 0.348582 0.602946 0.819000 0.192 Uiso 1 1 calc GR . . . .
C9 C 0.6526(5) 0.7819(4) 0.9936(4) 0.1234(11) Uani 1 1 d . . . . .
H9A H 0.598871 0.702368 1.039215 0.185 Uiso 1 1 calc GR . . . .
H9B H 0.621258 0.877120 1.012605 0.185 Uiso 1 1 calc GR . . . .
H9C H 0.774915 0.804528 1.028761 0.185 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 N2 C12 118.38(14) . . ?
C1 N2 C11 122.50(16) . . ?
C11 N2 C12 116.94(16) . . ?
C1 N1 C8 121.03(15) . . ?
C6 C5 C5 122.01(17) . 2_776 ?
C4 C5 C5 121.69(17) . 2_776 ?
C4 C5 C6 116.30(15) . . ?
C7 C2 C1 121.15(15) . . ?
C3 C2 C1 121.56(15) . . ?
C3 C2 C7 117.28(15) . . ?
N2 C1 C2 115.33(14) . . ?
N1 C1 N2 119.68(15) . . ?
N1 C1 C2 124.96(15) . . ?
C2 C7 H7 119.4 . . ?
C2 C7 C6 121.22(16) . . ?
C6 C7 H7 119.4 . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 121.92(16) . . ?
C7 C6 H6 119.0 . . ?
N1 C8 H8 109.7 . . ?
N1 C8 C10 109.5(2) . . ?
N1 C8 C9 108.3(2) . . ?
C10 C8 H8 109.7 . . ?
C10 C8 C9 110.1(2) . . ?
C9 C8 H8 109.7 . . ?
C5 C4 H4 119.0 . . ?
C5 C4 C3 121.94(17) . . ?
C3 C4 H4 119.0 . . ?
N2 C12 H12 106.9 . . ?
N2 C12 C14 111.20(19) . . ?
N2 C12 C13 112.05(19) . . ?
C14 C12 H12 106.9 . . ?
C13 C12 H12 106.9 . . ?
C13 C12 C14 112.4(2) . . ?
C2 C3 C4 121.33(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
N2 C1 1.380(2) . ?
N2 C12 1.470(2) . ?
N2 C11 1.440(3) . ?
N1 C1 1.274(2) . ?
N1 C8 1.458(2) . ?
C5 C5 1.488(3) 2_776 ?
C5 C6 1.382(2) . ?
C5 C4 1.378(2) . ?
C2 C1 1.498(2) . ?
C2 C7 1.377(2) . ?
C2 C3 1.373(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C8 C10 1.492(4) . ?
C8 C9 1.513(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(3) . ?
C12 H12 0.9800 . ?
C12 C14 1.515(4) . ?
C12 C13 1.487(4) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
