#------------------------------------------------------------------------------
#$Date: 2018-09-26 05:29:44 +0200 (Wed 26 de Sep de 2018) $
#$Revision: 211175 $
#$URL: svn://www.crystallography.net/cod/cif/8/00/01/8000128.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_8000128
loop_
_publ_author_name
'Ono, Yuki'
'Furuta, Hiroyuki'
_publ_section_title
;
 2-Picolinoylpyrrole: A New Entry to Metal-complexing Agent
;
_journal_issue                   7
_journal_name_full               'Chemistry Letters'
_journal_page_first              750
_journal_paper_doi               10.1246/cl.2006.750
_journal_volume                  35
_journal_year                    2006
_chemical_formula_sum            'C10 H8 N2 O'
_chemical_formula_weight         172.18
_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                 95.8120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9609(4)
_cell_length_b                   13.1442(8)
_cell_length_c                   10.6141(7)
_cell_measurement_reflns_used    3535
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      2.47
_cell_volume                     827.35(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4595
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  270
_diffrn_standards_number         112
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.9506
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS;Sheldrick, 1996'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0327
_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)+(0.0458P)²+0.2696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                1311
_reflns_number_total             1406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            35-750sup2.cif
_cod_data_source_block           p21n
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8000128
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
_atom_site_refinement_flags
C1 C 0.4945(2) 0.57168(10) 0.20386(12) 0.0254(3) Uani 1 1 d .
H2 H 0.6298 0.6088 0.1980 0.030 Uiso 1 1 calc R
C2 C 0.3309(2) 0.55331(10) 0.10566(12) 0.0266(3) Uani 1 1 d .
H3A H 0.3319 0.5758 0.0206 0.032 Uiso 1 1 calc R
C3 C 0.1630(2) 0.49548(10) 0.15418(12) 0.0240(3) Uani 1 1 d .
H4 H 0.0289 0.4712 0.1079 0.029 Uiso 1 1 calc R
C4 C 0.2271(2) 0.47975(9) 0.28236(12) 0.0210(3) Uani 1 1 d .
C5 C 0.1294(2) 0.42573(9) 0.38205(11) 0.0210(3) Uani 1 1 d .
C6 C -0.0856(2) 0.36619(9) 0.35462(12) 0.0215(3) Uani 1 1 d .
C7 C -0.1942(2) 0.33086(9) 0.45596(12) 0.0234(3) Uani 1 1 d .
H5 H -0.1348 0.3453 0.5405 0.028 Uiso 1 1 calc R
C8 C -0.3901(2) 0.27436(10) 0.43210(13) 0.0271(3) Uani 1 1 d .
H6 H -0.4658 0.2481 0.4997 0.033 Uiso 1 1 calc R
C9 C -0.4726(2) 0.25715(10) 0.30767(13) 0.0288(3) Uani 1 1 d .
H7 H -0.6075 0.2194 0.2877 0.035 Uiso 1 1 calc R
C10 C -0.3548(2) 0.29600(11) 0.21281(13) 0.0312(3) Uani 1 1 d .
H8 H -0.4136 0.2842 0.1275 0.037 Uiso 1 1 calc R
N1 N 0.43163(17) 0.52846(8) 0.30953(10) 0.0233(3) Uani 1 1 d .
H1 H 0.5090 0.5308 0.3846 0.028 Uiso 1 1 calc R
N2 N -0.16361(18) 0.34905(8) 0.23361(10) 0.0277(3) Uani 1 1 d .
O1 O 0.22172(14) 0.42654(7) 0.49188(8) 0.0247(2) 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
C1 0.0223(7) 0.0259(7) 0.0286(7) -0.0004(5) 0.0059(5) -0.0015(5)
C2 0.0296(7) 0.0287(7) 0.0215(6) 0.0029(5) 0.0028(5) 0.0001(5)
C3 0.0227(7) 0.0254(7) 0.0227(7) -0.0007(5) -0.0028(5) -0.0005(5)
C4 0.0187(6) 0.0211(6) 0.0227(7) -0.0024(5) -0.0008(5) 0.0008(5)
C5 0.0199(6) 0.0212(6) 0.0212(6) -0.0016(5) -0.0005(5) 0.0045(5)
C6 0.0212(6) 0.0187(6) 0.0240(7) 0.0013(5) -0.0007(5) 0.0032(5)
C7 0.0229(7) 0.0221(6) 0.0247(7) 0.0020(5) 0.0002(5) 0.0056(5)
C8 0.0244(7) 0.0232(7) 0.0348(8) 0.0055(5) 0.0075(5) 0.0032(5)
C9 0.0226(7) 0.0225(7) 0.0405(8) 0.0011(6) -0.0013(6) -0.0017(5)
C10 0.0317(8) 0.0294(7) 0.0308(8) 0.0005(6) -0.0057(6) -0.0080(6)
N1 0.0204(6) 0.0270(6) 0.0217(6) -0.0021(4) -0.0012(4) -0.0011(4)
N2 0.0287(6) 0.0277(6) 0.0257(6) 0.0010(5) -0.0028(5) -0.0071(5)
O1 0.0222(5) 0.0311(5) 0.0199(5) 0.0001(4) -0.0016(4) 0.0008(4)
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
N1 C1 C2 108.78(11)
C1 C2 C3 107.22(12)
C4 C3 C2 107.80(11)
N1 C4 C3 106.52(11)
N1 C4 C5 119.16(11)
C3 C4 C5 134.31(12)
O1 C5 C4 120.80(11)
O1 C5 C6 118.38(11)
C4 C5 C6 120.81(11)
N2 C6 C7 122.82(11)
N2 C6 C5 118.62(11)
C7 C6 C5 118.57(11)
C8 C7 C6 119.17(12)
C9 C8 C7 118.35(12)
C8 C9 C10 118.56(12)
N2 C10 C9 124.10(13)
C1 N1 C4 109.67(11)
C10 N2 C6 116.98(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3440(17)
C1 C2 1.3749(19)
C2 C3 1.3960(19)
C3 C4 1.3908(18)
C4 N1 1.3817(16)
C4 C5 1.4447(18)
C5 O1 1.2376(15)
C5 C6 1.5050(17)
C6 N2 1.3400(16)
C6 C7 1.3901(18)
C7 C8 1.3856(18)
C8 C9 1.3805(19)
C9 C10 1.382(2)
C10 N2 1.3354(17)
