#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/40/4504097.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_4504097
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         'C7 H5 N'
_chemical_formula_sum            'C7 H5 N'
_chemical_formula_weight         103.12
_chemical_name_common            3-Ethynylpyridine
_chemical_name_systematic
; 
 3-Ethynylpyridine 
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 96.23(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.8294(12)
_cell_length_b                   6.0334(17)
_cell_length_c                   12.139(5)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    135(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     278.81(17)
_computing_cell_refinement       'Siemens P3-PC diffractometer program'
_computing_data_collection       'Siemens P3-PC diffractometer program'
_computing_data_reduction        'Siemens XDISK'
_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. 5.03'
_diffrn_ambient_temperature      135(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nicolet R3m/V four circle diffractometer'
_diffrn_measurement_method       'Wyckoff scan mode'
_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  0.1473
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3484
_diffrn_reflns_theta_full        35.01
_diffrn_reflns_theta_max         35.01
_diffrn_reflns_theta_min         3.38
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             108
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0756
_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^)+(0.1419P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.1964
_reflns_number_gt                1892
_reflns_number_total             2034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060806wsi20061113_031338.cif
_cod_data_source_block           2
_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_cell_volume        278.80(16)
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               4504097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -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
N1 N -0.0075(4) 0.8526(2) -0.02725(11) 0.0300(3) Uani 1 1 d .
C2 C 0.1499(3) 0.7204(2) 0.05083(11) 0.0254(3) Uani 1 1 d .
H2 H 0.2302 0.5781 0.0288 0.030 Uiso 1 1 d R
C3 C 0.2086(3) 0.7777(2) 0.16332(11) 0.0207(3) Uani 1 1 d .
C4 C 0.0950(3) 0.9865(2) 0.19461(12) 0.0248(3) Uani 1 1 d .
H4 H 0.1302 1.0326 0.2707 0.030 Uiso 1 1 d R
C5 C -0.0678(4) 1.1255(2) 0.11392(13) 0.0278(3) Uani 1 1 d .
H5 H -0.1473 1.2698 0.1334 0.033 Uiso 1 1 d R
C6 C -0.1133(4) 1.0526(2) 0.00476(13) 0.0290(3) Uani 1 1 d .
H6 H -0.2277 1.1498 -0.0505 0.035 Uiso 1 1 d R
C7 C 0.3817(3) 0.6243(3) 0.24131(12) 0.0249(3) Uani 1 1 d .
C8 C 0.5298(4) 0.4918(3) 0.30290(13) 0.0294(3) Uani 1 1 d .
H8 H 0.6999 0.4142 0.3602 0.035 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 0.0416(7) 0.0223(5) 0.0253(5) 0.0011(5) 0.0000(5) -0.0002(5)
C2 0.0340(7) 0.0178(5) 0.0240(6) -0.0019(5) 0.0021(5) -0.0010(5)
C3 0.0237(5) 0.0159(4) 0.0227(5) 0.0006(4) 0.0038(4) -0.0023(4)
C4 0.0314(6) 0.0185(5) 0.0251(6) -0.0024(5) 0.0055(5) -0.0023(5)
C5 0.0326(7) 0.0169(5) 0.0348(7) -0.0001(5) 0.0077(5) 0.0006(5)
C6 0.0343(6) 0.0208(6) 0.0310(7) 0.0059(5) -0.0006(5) 0.0004(5)
C7 0.0272(5) 0.0217(5) 0.0260(6) -0.0005(4) 0.0036(4) -0.0033(4)
C8 0.0342(6) 0.0252(6) 0.0282(7) 0.0011(5) 0.0003(5) -0.0007(5)
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
C2 N1 C6 117.34(13)
N1 C2 C3 123.89(13)
N1 C2 H2 118.1
C3 C2 H2 118.0
C4 C3 C2 117.69(11)
C4 C3 C7 122.49(12)
C2 C3 C7 119.83(12)
C5 C4 C3 118.86(12)
C5 C4 H4 120.7
C3 C4 H4 120.5
C4 C5 C6 118.87(13)
C4 C5 H5 120.4
C6 C5 H5 120.8
N1 C6 C5 123.35(13)
N1 C6 H6 118.4
C5 C6 H6 118.2
C8 C7 C3 177.43(16)
C7 C8 H8 164.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3314(19)
N1 C6 1.344(2)
C2 C3 1.4028(17)
C2 H2 0.9600
C3 C4 1.3985(19)
C3 C7 1.434(2)
C4 C5 1.385(2)
C4 H4 0.9600
C5 C6 1.389(2)
C5 H5 0.9600
C6 H6 0.9600
C7 C8 1.195(2)
C8 H8 1.0145
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 161680
2 PubChem 186003
