#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/51/4025108.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_4025108
loop_
_publ_author_name
'Liyan Xing'
'Charline Wiegert'
'Anne Petitjean'
_publ_section_title
;
Stereochemical and Conformational Exchanges
inN,N'-Di(2-pyridyl)formamidines: An X-ray and1H NMR Study
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9513
_journal_page_last               9516
_journal_paper_doi               10.1021/jo9020453
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C11 H10 N4'
_chemical_formula_weight         198.23
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.561(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9881(19)
_cell_length_b                   4.3351(7)
_cell_length_c                   20.561(4)
_cell_measurement_reflns_used    3649
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      3.30
_cell_volume                     968.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5802
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                1503
_reflns_number_total             1911
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9020453_si_002.cif
_cod_data_source_block           ap04t
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               4025108
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.21824(9) -0.0867(2) 0.39925(5) 0.0342(3) Uani 1 1 d . . .
N2 N 0.08838(9) 0.2169(2) 0.45294(5) 0.0315(3) Uani 1 1 d . . .
H2N H 0.0160(13) 0.287(3) 0.4526(6) 0.043(4) Uiso 1 1 d . . .
N3 N 0.16555(8) 0.5298(2) 0.54018(5) 0.0321(3) Uani 1 1 d . . .
N4 N 0.26050(9) 0.7000(2) 0.64219(5) 0.0386(3) Uani 1 1 d . . .
C1 C 0.23093(12) -0.2904(3) 0.35164(6) 0.0368(3) Uani 1 1 d . . .
H1 H 0.3146(13) -0.357(3) 0.3482(6) 0.044(3) Uiso 1 1 d . . .
C2 C 0.13487(12) -0.4103(3) 0.30884(6) 0.0394(3) Uani 1 1 d . . .
H2 H 0.1504(11) -0.559(3) 0.2748(6) 0.042(3) Uiso 1 1 d . . .
C3 C 0.01654(12) -0.3168(3) 0.31564(6) 0.0386(3) Uani 1 1 d . . .
H3 H -0.0545(13) -0.389(3) 0.2875(7) 0.048(4) Uiso 1 1 d . . .
C4 C 0.00016(11) -0.1087(3) 0.36371(6) 0.0346(3) Uani 1 1 d . . .
H4 H -0.0764(12) -0.036(3) 0.3689(6) 0.040(3) Uiso 1 1 d . . .
C5 C 0.10351(10) 0.0017(2) 0.40434(5) 0.0300(3) Uani 1 1 d . . .
C6 C 0.18197(11) 0.3301(2) 0.49616(6) 0.0305(3) Uani 1 1 d . . .
H6 H 0.2607(10) 0.243(2) 0.4911(5) 0.027(3) Uiso 1 1 d . . .
C7 C 0.27268(10) 0.6418(2) 0.57957(6) 0.0317(3) Uani 1 1 d . . .
C8 C 0.38148(11) 0.7037(3) 0.55424(6) 0.0357(3) Uani 1 1 d . . .
H8 H 0.3825(10) 0.676(3) 0.5082(6) 0.034(3) Uiso 1 1 d . . .
C9 C 0.48061(12) 0.8221(3) 0.59573(7) 0.0410(3) Uani 1 1 d . . .
H9 H 0.5544(12) 0.871(3) 0.5782(6) 0.044(4) Uiso 1 1 d . . .
C10 C 0.46936(12) 0.8790(3) 0.66039(7) 0.0426(3) Uani 1 1 d . . .
H10 H 0.5354(12) 0.957(3) 0.6906(6) 0.050(4) Uiso 1 1 d . . .
C11 C 0.35859(12) 0.8164(3) 0.68104(7) 0.0432(3) Uani 1 1 d . . .
H11 H 0.3469(12) 0.853(3) 0.7276(7) 0.044(3) Uiso 1 1 d . . .
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
C5 N1 C1 116.60(10) . . ?
C6 N2 C5 123.72(10) . . ?
C6 N2 H2N 119.8(9) . . ?
C5 N2 H2N 116.3(9) . . ?
C6 N3 C7 116.31(10) . . ?
C7 N4 C11 117.22(11) . . ?
N1 C1 C2 124.35(12) . . ?
N1 C1 H1 116.7(7) . . ?
C2 C1 H1 119.0(7) . . ?
C1 C2 C3 117.85(12) . . ?
C1 C2 H2 120.4(7) . . ?
C3 C2 H2 121.8(7) . . ?
C4 C3 C2 119.38(12) . . ?
C4 C3 H3 118.0(8) . . ?
C2 C3 H3 122.6(8) . . ?
C3 C4 C5 118.47(11) . . ?
C3 C4 H4 122.1(8) . . ?
C5 C4 H4 119.4(8) . . ?
N1 C5 C4 123.35(11) . . ?
N1 C5 N2 117.53(10) . . ?
C4 C5 N2 119.11(10) . . ?
N3 C6 N2 122.45(11) . . ?
N3 C6 H6 124.3(6) . . ?
N2 C6 H6 113.2(6) . . ?
N4 C7 C8 122.37(11) . . ?
N4 C7 N3 114.99(10) . . ?
C8 C7 N3 122.56(11) . . ?
C9 C8 C7 118.77(12) . . ?
C9 C8 H8 122.3(7) . . ?
C7 C8 H8 118.8(7) . . ?
C10 C9 C8 119.23(12) . . ?
C10 C9 H9 121.7(8) . . ?
C8 C9 H9 119.0(8) . . ?
C11 C10 C9 118.31(12) . . ?
C11 C10 H10 119.8(8) . . ?
C9 C10 H10 121.9(8) . . ?
N4 C11 C10 124.09(12) . . ?
N4 C11 H11 115.2(8) . . ?
C10 C11 H11 120.8(8) . . ?
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 C5 1.3365(14) . ?
N1 C1 1.3408(16) . ?
N2 C6 1.3476(15) . ?
N2 C5 1.3950(15) . ?
N2 H2N 0.850(14) . ?
N3 C6 1.2847(15) . ?
N3 C7 1.4119(14) . ?
N4 C7 1.3383(15) . ?
N4 C11 1.3409(16) . ?
C1 C2 1.3720(18) . ?
C1 H1 0.976(14) . ?
C2 C3 1.3888(18) . ?
C2 H2 0.984(13) . ?
C3 C4 1.3697(17) . ?
C3 H3 0.952(14) . ?
C4 C5 1.3907(16) . ?
C4 H4 0.919(13) . ?
C6 H6 0.964(11) . ?
C7 C8 1.3992(16) . ?
C8 C9 1.3787(17) . ?
C8 H8 0.956(12) . ?
C9 C10 1.3757(18) . ?
C9 H9 0.959(13) . ?
C10 C11 1.3744(18) . ?
C10 H10 0.945(14) . ?
C11 H11 0.998(13) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N3 0.850(14) 2.173(15) 3.0212(14) 175.6(12) 3_566
C4 H4 N4 0.919(13) 2.475(14) 3.3545(16) 160.2(10) 3_566
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
C5 N1 C1 C2 0.01(17) . . . . ?
N1 C1 C2 C3 -0.60(18) . . . . ?
C1 C2 C3 C4 0.64(17) . . . . ?
C2 C3 C4 C5 -0.12(17) . . . . ?
C1 N1 C5 C4 0.57(16) . . . . ?
C1 N1 C5 N2 -179.08(10) . . . . ?
C3 C4 C5 N1 -0.51(17) . . . . ?
C3 C4 C5 N2 179.13(10) . . . . ?
C6 N2 C5 N1 -2.64(16) . . . . ?
C6 N2 C5 C4 177.70(10) . . . . ?
C7 N3 C6 N2 -176.32(10) . . . . ?
C5 N2 C6 N3 179.54(10) . . . . ?
C11 N4 C7 C8 -1.27(17) . . . . ?
C11 N4 C7 N3 -177.86(10) . . . . ?
C6 N3 C7 N4 -144.63(10) . . . . ?
C6 N3 C7 C8 38.79(15) . . . . ?
N4 C7 C8 C9 1.60(18) . . . . ?
N3 C7 C8 C9 177.93(11) . . . . ?
C7 C8 C9 C10 -0.74(19) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C7 N4 C11 C10 0.11(19) . . . . ?
C9 C10 C11 N4 0.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3564110
