#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/40/4504099.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_4504099
loop_
_publ_author_name
'Thalladi, Venkat R.'
'Dabros, Marta'
'Gehrke, Annette'
'Weiss, Hans-Christoph'
'Boese, Roland'
_publ_section_title
;
 Crystal Engineering with &#x22EE;C&#x2212;H&#x00B7;&#x00B7;&#x00B7;N and
 C&#x2212;H&#x00B7;&#x00B7;&#x00B7;N Hydrogen Bonds
;
_journal_issue                   4
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              598
_journal_paper_doi               10.1021/cg060806w
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C6 H4 N2'
_chemical_formula_sum            'C6 H4 N2'
_chemical_formula_weight         104.11
_chemical_name_common            5-Ethynylpyrimidine
_chemical_name_systematic
; 
 5-Ethynylpyrimidine 
;
_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                 94.547(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8710(6)
_cell_length_b                   13.890(2)
_cell_length_c                   10.2043(15)
_cell_measurement_reflns_used    1921
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.48
_cell_volume                     546.94(14)
_computing_cell_refinement       'Bruker AXS SAINT Ver. 6.0'
_computing_data_collection       'Bruker AXS SMART Ver. 5.054'
_computing_data_reduction        'Bruker AXS SAINT Ver. 6.0'
_computing_molecular_graphics    'Bruker AXS SHELXTL Ver. 5.10'
_computing_publication_material  'Bruker AXS SHELXTL Ver. 5.10'
_computing_structure_refinement  'Bruker AXS SHELXTL Ver. 5.10'
_computing_structure_solution    'Bruker AXS SHELXTL Ver. 5.10'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Siemens SMART CCD area detector system'
_diffrn_measurement_method
; 
Full sphere data collection in \w at 0.3\% scan width (300 frames with 
\F = 0\%), and in \F at 0.3\% scan width--four runs--(each with 600
frames with \w kept at 135, 143, 156 and 169 \%). 
;
_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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5105
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0622
_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/[\s^2^(Fo^2^)+(0.1195P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1858
_reflns_number_gt                902
_reflns_number_total             1312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060806wsi20061113_031338.cif
_cod_data_source_block           4
_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 'Empirical'
changed to 'empirical' 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_cell_volume        546.96(14)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4504099
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 0.7770(4) 0.16616(10) 0.41660(13) 0.0488(4) Uani 1 1 d .
N2 N 1.0641(4) 0.26567(11) 0.58095(14) 0.0504(5) Uani 1 1 d .
C2 C 0.9734(4) 0.18127(14) 0.52835(16) 0.0494(5) Uani 1 1 d .
H2 H 1.0587 0.1252 0.5755 0.059 Uiso 1 1 d R
C4 C 0.9462(4) 0.34276(13) 0.51508(16) 0.0472(5) Uani 1 1 d .
H4 H 1.0006 0.4052 0.5514 0.057 Uiso 1 1 d R
C5 C 0.7424(4) 0.33634(11) 0.39716(14) 0.0409(4) Uani 1 1 d .
C6 C 0.6636(4) 0.24445(12) 0.35234(15) 0.0435(4) Uani 1 1 d .
H6 H 0.5191 0.2366 0.2722 0.052 Uiso 1 1 d R
C7 C 0.6135(4) 0.42144(15) 0.32314(16) 0.0489(5) Uani 1 1 d .
C8 C 0.5171(4) 0.48229(15) 0.26665(17) 0.0502(5) Uani 1 1 d .
H8 H 0.4223 0.5478 0.2123 0.060 Uiso 1 1 d R
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 0.0483(8) 0.0494(10) 0.0481(7) 0.0011(6) 0.0009(6) -0.0024(6)
N2 0.0452(8) 0.0641(10) 0.0410(7) 0.0013(6) -0.0024(6) -0.0022(6)
C2 0.0435(9) 0.0577(11) 0.0468(8) 0.0091(7) 0.0030(7) 0.0008(7)
C4 0.0427(8) 0.0533(11) 0.0456(8) -0.0061(7) 0.0032(7) -0.0050(7)
C5 0.0343(8) 0.0489(10) 0.0398(7) 0.0007(6) 0.0058(6) 0.0001(6)
C6 0.0398(8) 0.0525(10) 0.0381(7) -0.0007(6) 0.0012(6) -0.0021(7)
C7 0.0399(8) 0.0584(11) 0.0485(8) -0.0107(8) 0.0039(7) -0.0081(8)
C8 0.0439(10) 0.0484(11) 0.0579(10) -0.0114(8) 0.0017(8) -0.0067(8)
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
C6 N1 C2 115.89(14)
C2 N2 C4 116.09(15)
N2 C2 N1 126.82(16)
N2 C2 H2 116.4
N1 C2 H2 116.8
N2 C4 C5 122.45(16)
N2 C4 H4 118.5
C5 C4 H4 119.0
C6 C5 C4 116.21(14)
C6 C5 C7 121.07(13)
C4 C5 C7 122.72(14)
N1 C6 C5 122.54(13)
N1 C6 H6 118.4
C5 C6 H6 119.0
C8 C7 C5 178.33(18)
C7 C8 H8 177.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.327(2)
N1 C2 1.336(2)
N2 C2 1.325(2)
N2 C4 1.326(2)
C2 H2 0.9599
C4 C5 1.388(2)
C4 H4 0.9600
C5 C6 1.382(2)
C5 C7 1.469(3)
C6 H6 0.9599
C7 C8 1.073(3)
C8 H8 1.1127
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1216997
2 PubChem 1475194
