#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150913.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_7150913
loop_
_publ_author_name
'West, Kara'
'Wang, Changsheng'
'Batsanov, Andrei S.'
'Bryce, Martin R.'
_publ_section_title
;
 Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl
 terminal bis(butadiynes)
 (HCC--CC--Ar--CC--CCH) and their
 applications in the synthesis of oligo(arylenebutadiynylene) molecular
 wires
;
_journal_issue                   11
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1934
_journal_page_last               1937
_journal_paper_doi               10.1039/b802968g
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C16 H11 N O'
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_chemical_name_common
6-(6-buta-1,3-diynyl-pyridin-3-yl)-2-methyl-hexa-3,5-diyn-2-ol
_chemical_name_systematic
;
6-(6-buta-1,3-diynyl-pyridin-3-yl)-2-methyl-hexa-3,5-diyn-2-ol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.79(1)
_cell_angle_beta                 77.87(1)
_cell_angle_gamma                77.99(1)
_cell_formula_units_Z            2
_cell_length_a                   5.7609(7)
_cell_length_b                   9.0756(10)
_cell_length_c                   12.6163(14)
_cell_measurement_reflns_used    3932
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      2.29
_cell_volume                     630.77(13)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7737
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker, 2003)'
_exptl_crystal_colour            off-white
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.1233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2626
_reflns_number_total             3464
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b802968g.txt
_cod_data_source_block           5d
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        630.77(12)
_cod_database_code               7150913
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O 0.40890(16) 0.33716(9) 0.25495(7) 0.0258(2) Uani 1 1 d . . .
H0 H 0.542(3) 0.271(2) 0.2769(14) 0.054(5) Uiso 1 1 d . . .
N1 N 1.18119(18) 0.84130(11) 0.67156(8) 0.0250(2) Uani 1 1 d . . .
C2 C 1.0411(2) 0.96719(13) 0.72327(9) 0.0227(2) Uani 1 1 d . . .
C3 C 0.8176(2) 1.03413(13) 0.69904(10) 0.0261(3) Uani 1 1 d . . .
H3 H 0.719(3) 1.1287(17) 0.7379(12) 0.035(4) Uiso 1 1 d . . .
C4 C 0.7332(2) 0.96912(13) 0.62171(10) 0.0249(2) Uani 1 1 d . . .
H4 H 0.581(3) 1.0131(17) 0.6040(12) 0.034(4) Uiso 1 1 d . . .
C5 C 0.8736(2) 0.83775(12) 0.56937(9) 0.0210(2) Uani 1 1 d . . .
C6 C 1.0976(2) 0.77951(13) 0.59696(9) 0.0239(2) Uani 1 1 d . . .
H6 H 1.199(3) 0.6867(16) 0.5615(11) 0.030(4) Uiso 1 1 d . . .
C7 C 1.1290(2) 1.02854(13) 0.80664(10) 0.0255(3) Uani 1 1 d . . .
C8 C 1.1874(2) 1.08108(13) 0.88073(10) 0.0254(2) Uani 1 1 d . . .
C9 C 1.2497(2) 1.13794(13) 0.96813(10) 0.0256(3) Uani 1 1 d . . .
C10 C 1.3011(2) 1.18397(14) 1.04575(11) 0.0282(3) Uani 1 1 d . . .
H10 H 1.338(3) 1.2192(18) 1.1076(13) 0.045(4) Uiso 1 1 d . . .
C11 C 0.7895(2) 0.76129(13) 0.49287(9) 0.0229(2) Uani 1 1 d . . .
C12 C 0.7139(2) 0.69436(13) 0.43106(9) 0.0232(2) Uani 1 1 d . . .
C13 C 0.6278(2) 0.61860(13) 0.36029(9) 0.0231(2) Uani 1 1 d . . .
C14 C 0.5565(2) 0.55154(13) 0.29743(9) 0.0225(2) Uani 1 1 d . . .
C15 C 0.4828(2) 0.47274(13) 0.21312(9) 0.0217(2) Uani 1 1 d . . .
C16 C 0.6975(2) 0.43614(15) 0.11757(10) 0.0283(3) Uani 1 1 d . . .
H161 H 0.750(3) 0.5292(17) 0.0862(12) 0.032(4) Uiso 1 1 d . . .
H162 H 0.649(3) 0.3812(18) 0.0612(13) 0.040(4) Uiso 1 1 d . . .
H163 H 0.832(3) 0.3711(18) 0.1413(12) 0.038(4) Uiso 1 1 d . . .
C17 C 0.2622(2) 0.57140(15) 0.17963(11) 0.0281(3) Uani 1 1 d . . .
H171 H 0.206(3) 0.5153(17) 0.1250(12) 0.034(4) Uiso 1 1 d . . .
H172 H 0.301(3) 0.6641(17) 0.1455(12) 0.032(4) Uiso 1 1 d . . .
H173 H 0.128(3) 0.5960(17) 0.2430(13) 0.040(4) 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'
O O 0.0106 0.0060 '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
C15 O H0 109.2(11) . . ?
C6 N1 C2 118.03(10) . . ?
N1 C2 C3 122.05(10) . . ?
N1 C2 C7 117.32(10) . . ?
C3 C2 C7 120.62(10) . . ?
C4 C3 C2 119.34(11) . . ?
C4 C3 H3 120.4(8) . . ?
C2 C3 H3 120.3(8) . . ?
C3 C4 C5 119.16(11) . . ?
C3 C4 H4 120.6(9) . . ?
C5 C4 H4 120.2(9) . . ?
C4 C5 C6 117.88(10) . . ?
C4 C5 C11 121.54(10) . . ?
C6 C5 C11 120.54(10) . . ?
N1 C6 C5 123.51(11) . . ?
N1 C6 H6 117.2(8) . . ?
C5 C6 H6 119.3(8) . . ?
C8 C7 C2 175.65(13) . . ?
C7 C8 C9 177.90(13) . . ?
C10 C9 C8 178.07(13) . . ?
C9 C10 H10 178.5(10) . . ?
C12 C11 C5 177.78(12) . . ?
C11 C12 C13 179.74(13) . . ?
C14 C13 C12 178.89(13) . . ?
C13 C14 C15 175.53(12) . . ?
O C15 C14 110.86(9) . . ?
O C15 C17 106.06(9) . . ?
C14 C15 C17 109.54(9) . . ?
O C15 C16 109.99(9) . . ?
C14 C15 C16 108.51(9) . . ?
C17 C15 C16 111.88(10) . . ?
C15 C16 H161 111.4(8) . . ?
C15 C16 H162 108.6(9) . . ?
H161 C16 H162 110.1(12) . . ?
C15 C16 H163 109.5(9) . . ?
H161 C16 H163 109.0(12) . . ?
H162 C16 H163 108.3(12) . . ?
C15 C17 H171 109.6(8) . . ?
C15 C17 H172 111.1(9) . . ?
H171 C17 H172 107.7(11) . . ?
C15 C17 H173 110.4(9) . . ?
H171 C17 H173 108.1(12) . . ?
H172 C17 H173 109.8(12) . . ?
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
O C15 1.4308(14) . ?
O H0 0.952(19) . ?
N1 C6 1.3325(14) . ?
N1 C2 1.3546(15) . ?
C2 C3 1.3947(17) . ?
C2 C7 1.4349(15) . ?
C3 C4 1.3783(16) . ?
C3 H3 1.007(15) . ?
C4 C5 1.3953(16) . ?
C4 H4 0.954(15) . ?
C5 C6 1.3987(16) . ?
C5 C11 1.4268(15) . ?
C6 H6 0.983(14) . ?
C7 C8 1.2033(16) . ?
C8 C9 1.3777(16) . ?
C9 C10 1.1941(16) . ?
C10 H10 0.934(17) . ?
C11 C12 1.2069(15) . ?
C12 C13 1.3753(15) . ?
C13 C14 1.2026(15) . ?
C14 C15 1.4825(15) . ?
C15 C17 1.5225(17) . ?
C15 C16 1.5254(17) . ?
C16 H161 0.995(15) . ?
C16 H162 1.000(16) . ?
C16 H163 0.964(16) . ?
C17 H171 1.015(15) . ?
C17 H172 0.977(15) . ?
C17 H173 0.985(16) . ?
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
O H0 N1 0.952(19) 1.929(19) 2.8761(14) 173.2(16) 2_766
C10 H10 O 0.934(17) 2.330(17) 3.2583(15) 172.8(14) 1_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653424
