#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:53:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/22/7212232.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_7212232
loop_
_publ_author_name
'Petitjean, Anne'
'Xing, Liyan'
'Wang, Ruiyao'
_publ_section_title
;
 Functional formamidines: pyridine substituents make an exception in the
 usual doubly hydrogen-bonded formamidine dimer
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              1397
_journal_paper_doi               10.1039/b922918c
_journal_volume                  12
_journal_year                    2010
_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            b922918c.txt
_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 2.4.2 from
2011-04-26.

'_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               7212232
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
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
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
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
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)
