
data_UMEX406_2
 

_publ_contact_author_name 
; 
Yasuhide Inokuma
; 
_publ_contact_author_address 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan)
; 
_publ_contact_author_email 
'inokuma@eng.hokudai.ac.jp'
  
_publ_contact_author_fax            +81-11-706-6557 
_publ_contact_author_phone          +81-11-706-6556 
_publ_requested_journal              'The Journal of Organic Chemistry'
_publ_section_title 
; 
Two-Step Transformation of Aliphatic Polyketones into Highly Pi-Conjugated Polyimines
; 
loop_ 
_publ_author_name 
_publ_author_address 

'Yumehiro Manabe' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Mitsuharu Uesaka' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
; 
'Tomoki Yoneda' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).
;
'Yasuhide Inokuma ' 
; 
Division of Applied Chemistry, Faculty of Engineering, Hokkaido University,
Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, (Japan).

Institute for Chemical Reaction Design and Discovery(WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo 001-0021, (Japan)
; 


_publ_section_abstract 
; 
  
; 
_publ_section_references 
; 
   Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. 
   SHELXT Version 2018/2 
  
   Sheldrick, G.M. (2015) SHELXL Version 2018/3, Acta Cryst. C71, 3-8. 
; 
  

_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C14 H20 N4' 
_chemical_formula_sum
 'C14 H20 N4' 
_chemical_formula_weight          244.34

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    6.1286(4)
_cell_length_b                    12.4667(8)
_cell_length_c                    9.5271(8)
_cell_angle_alpha                 90
_cell_angle_beta                  104.044(8)
_cell_angle_gamma                 90
_cell_volume                      706.15(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     2413
_cell_measurement_theta_min       3.2780
_cell_measurement_theta_max       28.4990
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'brown'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.149          
_exptl_crystal_F_000              264
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.450
_exptl_crystal_size_mid           0.310
_exptl_crystal_size_min           0.090
_exptl_absorpt_coefficient_mu     0.071
_shelx_estimated_absorpt_T_min    0.969
_shelx_estimated_absorpt_T_max    0.994
_exptl_absorpt_correction_T_min   0.43754
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source 'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type 'Rigaku (Mo) X-ray DW Source'
_diffrn_radiation_probe x-ray
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             5932
_diffrn_reflns_av_unetI/netI      0.0280
_diffrn_reflns_av_R_equivalents   0.0324
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.743
_diffrn_reflns_theta_max          25.990
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.989
_diffrn_measured_fraction_theta_full  0.994
_diffrn_reflns_Laue_measured_fraction_max    0.989
_diffrn_reflns_Laue_measured_fraction_full   0.994
_diffrn_reflns_point_group_measured_fraction_max   0.989
_diffrn_reflns_point_group_measured_fraction_full  0.994
_reflns_number_total              1381
_reflns_number_gt                 1149
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0485P)²+0.2053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          1381
_refine_ls_number_parameters      85
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0548
_refine_ls_R_factor_gt            0.0439
_refine_ls_wR_factor_ref          0.1106
_refine_ls_wR_factor_gt           0.1046
_refine_ls_goodness_of_fit_ref    1.100
_refine_ls_restrained_S_all       1.100
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.6525(2) 0.58927(9) 0.74986(13) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.7409(2) 0.54555(10) 0.63483(14) 0.0333(3) Uani 1 1 d . . . . .
C3 C 0.6729(2) 0.40384(11) 0.77782(15) 0.0237(3) Uani 1 1 d . . . . .
C4 C 0.6117(2) 0.51127(10) 0.82906(15) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.7494(2) 0.44280(11) 0.64864(15) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.5217(2) 0.53566(11) 0.95262(15) 0.0262(3) Uani 1 1 d . . . . .
H10 H 0.490547 0.608824 0.967774 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4741(2) 0.32596(12) 0.73262(16) 0.0309(4) Uani 1 1 d . . . . .
H1 H 0.411956 0.310712 0.816074 0.046 Uiso 1 1 calc R U . . .
H2 H 0.525957 0.259025 0.697559 0.046 Uiso 1 1 calc R U . . .
H3 H 0.357590 0.358442 0.655389 0.046 Uiso 1 1 calc R U . . .
C7 C 0.8702(2) 0.35224(12) 0.88773(16) 0.0337(4) Uani 1 1 d . . . . .
H4 H 0.995730 0.403074 0.912028 0.051 Uiso 1 1 calc R U . . .
H5 H 0.918471 0.287302 0.845735 0.051 Uiso 1 1 calc R U . . .
H6 H 0.822405 0.333425 0.975582 0.051 Uiso 1 1 calc R U . . .
C1 C 0.8239(3) 0.37064(13) 0.54490(17) 0.0352(4) Uani 1 1 d . . . . .
H7 H 0.691900 0.339130 0.478486 0.053 Uiso 1 1 calc R U . . .
H8 H 0.918186 0.313349 0.598289 0.053 Uiso 1 1 calc R U . . .
H9 H 0.910523 0.411920 0.489594 0.053 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C4 1.2919(18) . ?
N2 N1 1.4421(17) . ?
N1 C2 1.2875(19) . ?
C3 C2 1.5003(19) . ?
C3 C4 1.5038(19) . ?
C3 C6 1.5352(19) . ?
C3 C7 1.5358(19) . ?
C4 C5 1.449(2) . ?
C2 C1 1.488(2) . ?
C5 C5 1.339(3) 3_667 ?
 
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
C4 N2 N1 108.73(11) . . ?
C2 N1 N2 108.16(11) . . ?
C2 C3 C4 97.47(11) . . ?
C2 C3 C6 111.06(11) . . ?
C4 C3 C6 114.27(11) . . ?
C2 C3 C7 110.10(11) . . ?
C4 C3 C7 111.64(12) . . ?
C6 C3 C7 111.49(12) . . ?
N2 C4 C5 118.85(13) . . ?
N2 C4 C3 112.46(13) . . ?
C5 C4 C3 128.67(12) . . ?
N1 C2 C1 123.03(13) . . ?
N1 C2 C3 113.15(12) . . ?
C1 C2 C3 123.82(13) . . ?
C5 C5 C4 125.85(17) 3_667 . ?
 
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
C4 N2 N1 C2 0.22(16) . . . . ?
N1 N2 C4 C5 179.85(12) . . . . ?
N1 N2 C4 C3 1.12(16) . . . . ?
C2 C3 C4 N2 -1.78(14) . . . . ?
C6 C3 C4 N2 -118.96(14) . . . . ?
C7 C3 C4 N2 113.36(14) . . . . ?
C2 C3 C4 C5 179.64(13) . . . . ?
C6 C3 C4 C5 62.46(19) . . . . ?
C7 C3 C4 C5 -65.22(18) . . . . ?
N2 N1 C2 C1 177.47(12) . . . . ?
N2 N1 C2 C3 -1.47(16) . . . . ?
C4 C3 C2 N1 1.94(15) . . . . ?
C6 C3 C2 N1 121.60(13) . . . . ?
C7 C3 C2 N1 -114.42(14) . . . . ?
C4 C3 C2 C1 -176.99(13) . . . . ?
C6 C3 C2 C1 -57.34(17) . . . . ?
C7 C3 C2 C1 66.65(17) . . . . ?
N2 C4 C5 C5 -177.51(17) . . . 3_667 ?
C3 C4 C5 C5 1.0(3) . . . 3_667 ?
 
_refine_diff_density_max    0.252
_refine_diff_density_min   -0.129
_refine_diff_density_rms    0.036







