#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:52:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180402 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/71/7207111.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_7207111
loop_
_publ_author_name
'Shivakumar, Kota'
'Vidyasagar, Adiyala'
'Naidu, Andra'
'Gonnade, Rajesh G.'
'Sureshan, Kana M.'
_publ_section_title
;
 Strength from weakness: The role of CH…N hydrogen bond in the
 formation of wave-like topology in crystals of aza-heterocycles
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              519
_journal_paper_doi               10.1039/c1ce05997a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C10 H5 N5'
_chemical_formula_sum            'C10 H5 N5'
_chemical_formula_weight         195.19
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.714(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.353(4)
_cell_length_b                   13.472(8)
_cell_length_c                   9.327(6)
_cell_measurement_reflns_used    437
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      19.06
_cell_measurement_theta_min      2.757
_cell_volume                     875.1(9)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega Scan'
_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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4260
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0763
_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)+(0.0662P)²+0.1648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                994
_reflns_number_total             1545
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05997a.txt
_cod_data_source_block           kms11
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7207111
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.7528(4) 0.8514(2) 0.4778(3) 0.0342(8) Uani 1 1 d .
N2 N 0.6259(5) 0.7373(2) 0.3107(3) 0.0466(9) Uani 1 1 d .
N3 N 0.7465(5) 0.6961(2) 0.4390(4) 0.0521(9) Uani 1 1 d .
N4 N 0.8244(4) 0.7630(2) 0.5413(3) 0.0450(8) Uani 1 1 d .
N5 N 0.3042(5) 0.8810(3) -0.0206(4) 0.0627(11) Uani 1 1 d .
C2 C 0.6318(5) 0.8336(3) 0.3372(4) 0.0358(9) Uani 1 1 d .
C3 C 0.5396(5) 0.9158(3) 0.2451(4) 0.0342(9) Uani 1 1 d .
C4 C 0.5775(5) 1.0082(3) 0.3020(4) 0.0398(9) Uani 1 1 d .
H4 H 0.5196 1.0620 0.2422 0.048 Uiso 1 1 calc R
C5 C 0.7471(5) 1.1209(3) 0.5149(4) 0.0457(10) Uani 1 1 d .
H5 H 0.6911 1.1760 0.4574 0.055 Uiso 1 1 calc R
C6 C 0.8694(6) 1.1342(3) 0.6592(4) 0.0499(11) Uani 1 1 d .
H6 H 0.8959 1.1980 0.6985 0.060 Uiso 1 1 calc R
C7 C 0.9538(5) 1.0533(3) 0.7474(4) 0.0477(11) Uani 1 1 d .
H7 H 1.0353 1.0634 0.8456 0.057 Uiso 1 1 calc R
C8 C 0.9187(5) 0.9581(3) 0.6914(4) 0.0418(10) Uani 1 1 d .
H8 H 0.9763 0.9038 0.7500 0.050 Uiso 1 1 calc R
C9 C 0.7953(5) 0.9455(2) 0.5453(4) 0.0346(9) Uani 1 1 d .
C10 C 0.7051(5) 1.0259(2) 0.4526(4) 0.0339(9) Uani 1 1 d .
C11 C 0.4091(5) 0.8962(3) 0.0961(4) 0.0428(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0329(18) 0.0331(18) 0.0343(17) 0.0035(13) 0.0077(14) 0.0024(13)
N2 0.056(2) 0.0337(19) 0.0453(19) -0.0022(15) 0.0086(17) -0.0022(15)
N3 0.063(2) 0.0325(19) 0.055(2) 0.0059(16) 0.0108(18) 0.0014(16)
N4 0.049(2) 0.0367(19) 0.0474(19) 0.0073(16) 0.0121(16) 0.0073(16)
N5 0.061(2) 0.072(3) 0.042(2) 0.0018(18) -0.0032(19) 0.0009(19)
C2 0.036(2) 0.035(2) 0.037(2) -0.0023(16) 0.0109(17) -0.0069(16)
C3 0.030(2) 0.039(2) 0.0308(19) 0.0039(16) 0.0058(16) -0.0020(16)
C4 0.044(2) 0.037(2) 0.037(2) 0.0061(17) 0.0112(18) 0.0020(18)
C5 0.048(3) 0.033(2) 0.056(3) -0.0010(18) 0.017(2) -0.0045(18)
C6 0.049(3) 0.049(3) 0.052(3) -0.017(2) 0.018(2) -0.010(2)
C7 0.041(3) 0.061(3) 0.039(2) -0.010(2) 0.0101(19) -0.005(2)
C8 0.034(2) 0.046(2) 0.040(2) -0.0015(18) 0.0042(18) 0.0046(18)
C9 0.027(2) 0.036(2) 0.039(2) -0.0008(17) 0.0086(17) -0.0026(16)
C10 0.031(2) 0.035(2) 0.036(2) 0.0027(16) 0.0121(17) -0.0020(16)
C11 0.041(2) 0.045(2) 0.038(2) 0.0049(18) 0.008(2) 0.0040(18)
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 N4 108.1(3)
C2 N1 C9 125.3(3)
N4 N1 C9 126.6(3)
C2 N2 N3 105.3(3)
N4 N3 N2 111.8(3)
N3 N4 N1 105.6(3)
N2 C2 N1 109.2(3)
N2 C2 C3 131.9(3)
N1 C2 C3 118.9(3)
C4 C3 C2 118.7(3)
C4 C3 C11 122.7(3)
C2 C3 C11 118.6(3)
C3 C4 C10 121.7(3)
C6 C5 C10 121.0(4)
C5 C6 C7 120.5(4)
C8 C7 C6 120.9(4)
C7 C8 C9 118.1(3)
C8 C9 N1 122.2(3)
C8 C9 C10 122.7(3)
N1 C9 C10 115.1(3)
C5 C10 C9 116.8(3)
C5 C10 C4 123.0(3)
C9 C10 C4 120.2(3)
N5 C11 C3 179.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.349(4)
N1 N4 1.358(4)
N1 C9 1.406(4)
N2 C2 1.320(4)
N2 N3 1.358(4)
N3 N4 1.304(4)
N5 C11 1.133(4)
C2 C3 1.431(5)
C3 C4 1.347(5)
C3 C11 1.437(5)
C4 C10 1.437(5)
C5 C6 1.370(5)
C5 C10 1.399(5)
C6 C7 1.387(5)
C7 C8 1.377(5)
C8 C9 1.384(5)
C9 C10 1.411(5)
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
C2 N2 N3 N4 0.1(4)
N2 N3 N4 N1 -0.2(4)
C2 N1 N4 N3 0.2(4)
C9 N1 N4 N3 -180.0(3)
N3 N2 C2 N1 0.1(4)
N3 N2 C2 C3 178.6(4)
N4 N1 C2 N2 -0.2(4)
C9 N1 C2 N2 -180.0(3)
N4 N1 C2 C3 -178.9(3)
C9 N1 C2 C3 1.3(5)
N2 C2 C3 C4 -178.1(4)
N1 C2 C3 C4 0.2(5)
N2 C2 C3 C11 2.3(6)
N1 C2 C3 C11 -179.3(3)
C2 C3 C4 C10 -1.0(5)
C11 C3 C4 C10 178.5(3)
C10 C5 C6 C7 -0.3(6)
C5 C6 C7 C8 0.8(6)
C6 C7 C8 C9 -0.7(6)
C7 C8 C9 N1 179.1(3)
C7 C8 C9 C10 0.0(5)
C2 N1 C9 C8 178.9(3)
N4 N1 C9 C8 -0.9(5)
C2 N1 C9 C10 -2.0(5)
N4 N1 C9 C10 178.3(3)
C6 C5 C10 C9 -0.3(5)
C6 C5 C10 C4 179.9(3)
C8 C9 C10 C5 0.4(5)
N1 C9 C10 C5 -178.7(3)
C8 C9 C10 C4 -179.7(3)
N1 C9 C10 C4 1.1(5)
C3 C4 C10 C5 -179.9(4)
C3 C4 C10 C9 0.3(5)
