#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:22:04 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222589 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034029.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_4034029
loop_
_publ_author_name
'Manabe, Yumehiro'
'Uesaka, Mitsuharu'
'Yoneda, Tomoki'
'Inokuma, Yasuhide'
_publ_section_title
;
 Two-Step Transformation of Aliphatic Polyketones into π-Conjugated
 Polyimines.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9957
_journal_page_last               9964
_journal_paper_doi               10.1021/acs.joc.9b01119
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H20 N4'
_chemical_formula_sum            'C14 H20 N4'
_chemical_formula_weight         244.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.044(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1286(4)
_cell_length_b                   12.4667(8)
_cell_length_c                   9.5271(8)
_cell_measurement_reflns_used    2413
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.4990
_cell_measurement_theta_min      3.2780
_cell_volume                     706.15(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5932
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_min         2.743
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43754
_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_crystal_colour            brown
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0439
_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)+(0.0485P)²+0.2053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1149
_reflns_number_total             1381
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01119_si_003.cif
_cod_data_source_block           UMEX406_2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034029
_shelx_shelxl_version_number     2018/3
_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_min   0.969
_shelx_estimated_absorpt_t_max   0.994
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'
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
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
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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_4
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
