#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:51:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180319 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/33/7153312.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_7153312
loop_
_publ_author_name
'Laroche, Christophe'
'Li, Jing'
'Gonzales, Cristina'
'David, Wendi M.'
'Kerwin, Sean M.'
_publ_section_title
;
 Cyclization kinetics and biological evaluation of an anticancer
 1,2-dialkynylimidazole.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1535
_journal_page_last               1539
_journal_paper_doi               10.1039/b925261d
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.138(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9680(4)
_cell_length_b                   10.7628(10)
_cell_length_c                   27.402(2)
_cell_measurement_reflns_used    1825
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     1170.02(18)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            3467
_diffrn_reflns_theta_full        25.21
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       laths
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0092(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0053P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                969
_reflns_number_total             2039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b925261d.txt
_cod_data_source_block           lar1
_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.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7153312
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.2512(4) 0.27857(12) 0.12815(6) 0.0651(5) Uani 1 1 d
N1 N 0.7911(5) 0.31651(15) 0.44476(7) 0.0590(6) Uani 1 1 d
N2 N 0.9260(5) 0.11677(16) 0.44140(8) 0.0719(7) Uani 1 1 d
C1 C 0.8067(6) 0.21117(19) 0.41621(8) 0.0571(7) Uani 1 1 d
C2 C 0.9128(7) 0.2841(3) 0.49042(10) 0.0700(8) Uani 1 1 d
C3 C 0.9935(7) 0.1631(2) 0.48720(11) 0.0763(8) Uani 1 1 d
C4 C 0.7068(6) 0.21452(19) 0.36627(10) 0.0609(7) Uani 1 1 d
C5 C 0.6260(6) 0.22464(18) 0.32415(9) 0.0585(7) Uani 1 1 d
C6 C 0.5286(5) 0.23905(18) 0.27414(8) 0.0514(6) Uani 1 1 d
C7 C 0.3659(6) 0.3469(2) 0.25839(9) 0.0569(7) Uani 1 1 d
C8 C 0.2740(6) 0.36430(19) 0.21001(9) 0.0540(7) Uani 1 1 d
C9 C 0.3384(5) 0.27211(18) 0.17652(8) 0.0497(6) Uani 1 1 d
C10 C 0.5018(6) 0.1639(2) 0.19149(9) 0.0549(7) Uani 1 1 d
C11 C 0.5969(6) 0.14863(19) 0.23949(9) 0.0545(6) Uani 1 1 d
C12 C 0.0790(9) 0.3895(3) 0.11116(13) 0.0738(9) Uani 1 1 d
C13 C 0.6673(6) 0.4297(2) 0.43030(9) 0.0655(7) Uani 1 1 d
C14 C 0.5634(7) 0.5256(2) 0.41698(10) 0.0840(9) Uani 1 1 d
H2 H 0.929(6) 0.3409(19) 0.5178(10) 0.097(9) Uiso 1 1 d
H3 H 1.076(5) 0.1082(18) 0.5132(9) 0.080(7) Uiso 1 1 d
H7 H 0.320(5) 0.4107(15) 0.2828(8) 0.062(6) Uiso 1 1 d
H8 H 0.161(4) 0.4433(15) 0.2002(7) 0.058(6) Uiso 1 1 d
H10 H 0.536(5) 0.1031(15) 0.1682(8) 0.056(6) Uiso 1 1 d
H11 H 0.719(4) 0.0695(15) 0.2499(7) 0.056(6) Uiso 1 1 d
H12A H 0.029(6) 0.3710(19) 0.0779(10) 0.086(9) Uiso 1 1 d
H12B H 0.236(6) 0.4687(19) 0.1166(9) 0.110(9) Uiso 1 1 d
H12C H -0.130(7) 0.402(2) 0.1287(11) 0.119(13) Uiso 1 1 d
H14 H 0.477(6) 0.608(2) 0.4064(10) 0.113(9) 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
C9 O1 C12 117.6(2)
C13 N1 C2 127.3(2)
C13 N1 C1 125.9(2)
C2 N1 C1 106.73(18)
C1 N2 C3 105.15(18)
N2 C1 N1 111.0(2)
N2 C1 C4 128.2(2)
N1 C1 C4 120.8(2)
C3 C2 N1 105.4(2)
C3 C2 H2 130.6(14)
N1 C2 H2 124.0(14)
C2 C3 N2 111.7(2)
C2 C3 H3 127.9(13)
N2 C3 H3 120.2(12)
C5 C4 C1 176.2(2)
C4 C5 C6 179.0(2)
C11 C6 C7 117.9(2)
C11 C6 C5 121.9(2)
C7 C6 C5 120.3(2)
C8 C7 C6 121.5(2)
C8 C7 H7 120.9(11)
C6 C7 H7 117.6(11)
C7 C8 C9 119.5(2)
C7 C8 H8 118.9(11)
C9 C8 H8 121.6(11)
O1 C9 C8 124.26(19)
O1 C9 C10 115.9(2)
C8 C9 C10 119.8(2)
C11 C10 C9 120.1(2)
C11 C10 H10 122.3(12)
C9 C10 H10 117.5(12)
C10 C11 C6 121.1(2)
C10 C11 H11 119.3(10)
C6 C11 H11 119.5(10)
O1 C12 H12A 103.0(13)
O1 C12 H12B 110.1(11)
H12A C12 H12B 114(2)
O1 C12 H12C 110.7(15)
H12A C12 H12C 110(2)
H12B C12 H12C 109(2)
C14 C13 N1 178.6(3)
C13 C14 H14 178.6(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.365(2)
O1 C12 1.448(3)
N1 C13 1.369(3)
N1 C2 1.377(3)
N1 C1 1.380(3)
N2 C1 1.311(2)
N2 C3 1.372(3)
C1 C4 1.418(3)
C2 C3 1.344(3)
C2 H2 0.97(2)
C3 H3 0.98(2)
C4 C5 1.197(3)
C5 C6 1.425(3)
C6 C11 1.390(3)
C6 C7 1.392(3)
C7 C8 1.381(3)
C7 H7 0.978(19)
C8 C9 1.379(3)
C8 H8 0.996(16)
C9 C10 1.390(3)
C10 C11 1.371(3)
C10 H10 0.926(18)
C11 H11 1.019(16)
C12 H12A 0.95(3)
C12 H12B 1.06(2)
C12 H12C 0.98(3)
C13 C14 1.167(3)
C14 H14 0.99(2)
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
C3 N2 C1 N1 -0.9(3)
C3 N2 C1 C4 178.0(3)
C13 N1 C1 N2 -177.4(2)
C2 N1 C1 N2 0.7(3)
C13 N1 C1 C4 3.6(4)
C2 N1 C1 C4 -178.3(2)
C13 N1 C2 C3 177.9(2)
C1 N1 C2 C3 -0.1(3)
N1 C2 C3 N2 -0.4(3)
C1 N2 C3 C2 0.8(3)
N2 C1 C4 C5 -156(4)
N1 C1 C4 C5 23(4)
C1 C4 C5 C6 -21(18)
C4 C5 C6 C11 165(15)
C4 C5 C6 C7 -14(15)
C11 C6 C7 C8 0.1(3)
C5 C6 C7 C8 178.9(2)
C6 C7 C8 C9 1.3(3)
C12 O1 C9 C8 -0.2(3)
C12 O1 C9 C10 179.7(2)
C7 C8 C9 O1 178.4(2)
C7 C8 C9 C10 -1.5(3)
O1 C9 C10 C11 -179.5(2)
C8 C9 C10 C11 0.4(3)
C9 C10 C11 C6 1.0(4)
C7 C6 C11 C10 -1.2(3)
C5 C6 C11 C10 -180.0(2)
C2 N1 C13 C14 157(11)
C1 N1 C13 C14 -26(11)
