#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/50/2225026.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225026
loop_
_publ_author_name
'Journot, Guillaume'
'Neier, Reinhard'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 4,4-Bis(1H-pyrrol-2-yl)pentanol
;
_journal_coeditor_code           IS2505
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o393
_journal_paper_doi               10.1107/S1600536809054269
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H18 N2 O'
_chemical_formula_moiety         'C13 H18 N2 O'
_chemical_formula_sum            'C13 H18 N2 O'
_chemical_formula_weight         218.29
_chemical_name_systematic
;
4,4-Bis(1H-pyrrol-2-yl)pentanol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 101.530(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4721(15)
_cell_length_b                   8.2111(9)
_cell_length_c                   8.7120(15)
_cell_measurement_reflns_used    5671
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      2.39
_cell_volume                     593.82(16)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2009)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'φ ans 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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6119
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.160
_refine_ls_abs_structure_details 'none; 1239 Friedel pairs merged'
_refine_ls_extinction_coef       0.108(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1701
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0303
_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)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                1518
_reflns_number_total             1701
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2505.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2225026
_cod_database_fobs_code          2225026
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.41371(13) 1.28786(14) 0.88057(13) 0.0300(3) Uani . . 1.000
N N1 0.24737(14) 0.55996(17) 0.99568(13) 0.0244(3) Uani . . 1.000
N N2 0.48148(15) 0.66563(17) 0.79634(16) 0.0281(3) Uani . . 1.000
C C1 0.18516(15) 0.69959(18) 0.92203(15) 0.0220(3) Uani . . 1.000
C C2 0.12554(18) 0.7921(2) 1.02911(17) 0.0293(4) Uani . . 1.000
C C3 0.15673(18) 0.7047(2) 1.17356(17) 0.0318(4) Uani . . 1.000
C C4 0.23207(17) 0.5631(2) 1.14900(16) 0.0286(4) Uani . . 1.000
C C5 0.33030(17) 0.64998(19) 0.70462(15) 0.0248(4) Uani . . 1.000
C C6 0.3443(2) 0.5545(3) 0.57848(18) 0.0409(5) Uani . . 1.000
C C7 0.5085(3) 0.5108(3) 0.5947(2) 0.0518(7) Uani . . 1.000
C C8 0.5900(2) 0.5804(3) 0.7302(2) 0.0419(6) Uani . . 1.000
C C9 0.18427(16) 0.72822(17) 0.74921(15) 0.0221(3) Uani . . 1.000
C C10 0.17922(17) 0.91270(19) 0.71418(16) 0.0244(4) Uani . . 1.000
C C11 0.32247(16) 1.01255(19) 0.79998(16) 0.0248(4) Uani . . 1.000
C C12 0.2876(2) 1.1921(2) 0.7865(2) 0.0398(5) Uani . . 1.000
C C13 0.03085(19) 0.6525(2) 0.65082(18) 0.0349(4) Uani . . 1.000
H H1N 0.297(2) 0.482(3) 0.955(2) 0.037(5) Uiso . . 1.000
H H1O 0.485(4) 1.307(4) 0.823(3) 0.073(9) Uiso . . 1.000
H H2 0.07350 0.89480 1.01050 0.0350 Uiso calc R 1.000
H H2N 0.504(2) 0.709(3) 0.893(2) 0.034(5) Uiso . . 1.000
H H3 0.12990 0.73890 1.26930 0.0380 Uiso calc R 1.000
H H4 0.26760 0.48110 1.22500 0.0340 Uiso calc R 1.000
H H6 0.25910 0.52330 0.49530 0.0490 Uiso calc R 1.000
H H7 0.55360 0.44540 0.52450 0.0620 Uiso calc R 1.000
H H8 0.70230 0.57120 0.77130 0.0500 Uiso calc R 1.000
H H10A 0.17120 0.92760 0.60010 0.0290 Uiso calc R 1.000
H H10B 0.07980 0.95800 0.74090 0.0290 Uiso calc R 1.000
H H11A 0.34710 0.98110 0.91190 0.0300 Uiso calc R 1.000
H H11B 0.41830 0.98810 0.75510 0.0300 Uiso calc R 1.000
H H12A 0.27480 1.22540 0.67550 0.0480 Uiso calc R 1.000
H H12B 0.18470 1.21430 0.82010 0.0480 Uiso calc R 1.000
H H13A -0.06410 0.70130 0.68090 0.0520 Uiso calc R 1.000
H H13B 0.03100 0.53480 0.66940 0.0520 Uiso calc R 1.000
H H13C 0.02780 0.67330 0.53950 0.0520 Uiso calc R 1.000
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O1 H1O . . . 106.9(19) no
C1 N1 C4 . . . 109.86(13) no
C5 N2 C8 . . . 109.48(13) no
C4 N1 H1N . . . 123.7(13) no
C1 N1 H1N . . . 126.3(13) no
C5 N2 H2N . . . 125.5(11) no
C8 N2 H2N . . . 124.2(12) no
N1 C1 C2 . . . 107.72(12) no
N1 C1 C9 . . . 121.26(12) no
C2 C1 C9 . . . 130.98(13) no
C1 C2 C3 . . . 106.99(14) no
C2 C3 C4 . . . 107.48(13) no
N1 C4 C3 . . . 107.94(13) no
N2 C5 C6 . . . 107.40(14) no
N2 C5 C9 . . . 121.77(12) no
C6 C5 C9 . . . 130.82(13) no
C5 C6 C7 . . . 107.75(15) no
C6 C7 C8 . . . 107.25(18) no
N2 C8 C7 . . . 108.11(17) no
C1 C9 C10 . . . 109.96(11) no
C1 C9 C5 . . . 110.24(11) no
C5 C9 C10 . . . 110.97(12) no
C5 C9 C13 . . . 109.20(12) no
C1 C9 C13 . . . 108.99(11) no
C10 C9 C13 . . . 107.43(11) no
C9 C10 C11 . . . 116.18(12) no
C10 C11 C12 . . . 111.28(12) no
O1 C12 C11 . . . 112.24(13) no
C1 C2 H2 . . . 127.00 no
C3 C2 H2 . . . 126.00 no
C2 C3 H3 . . . 126.00 no
C4 C3 H3 . . . 126.00 no
N1 C4 H4 . . . 126.00 no
C3 C4 H4 . . . 126.00 no
C5 C6 H6 . . . 126.00 no
C7 C6 H6 . . . 126.00 no
C6 C7 H7 . . . 126.00 no
C8 C7 H7 . . . 126.00 no
N2 C8 H8 . . . 126.00 no
C7 C8 H8 . . . 126.00 no
C9 C10 H10A . . . 108.00 no
C9 C10 H10B . . . 108.00 no
C11 C10 H10A . . . 108.00 no
C11 C10 H10B . . . 108.00 no
H10A C10 H10B . . . 107.00 no
C10 C11 H11A . . . 109.00 no
C10 C11 H11B . . . 109.00 no
C12 C11 H11A . . . 109.00 no
C12 C11 H11B . . . 109.00 no
H11A C11 H11B . . . 108.00 no
O1 C12 H12A . . . 109.00 no
O1 C12 H12B . . . 109.00 no
C11 C12 H12A . . . 109.00 no
C11 C12 H12B . . . 109.00 no
H12A C12 H12B . . . 108.00 no
C9 C13 H13A . . . 109.00 no
C9 C13 H13B . . . 109.00 no
C9 C13 H13C . . . 109.00 no
H13A C13 H13B . . . 109.00 no
H13A C13 H13C . . . 109.00 no
H13B C13 H13C . . . 110.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . . 1.443(2) no
O1 H1O . . 0.87(3) no
N1 C1 . . 1.367(2) no
N1 C4 . . 1.3678(18) no
N2 C8 . . 1.371(2) no
N2 C5 . . 1.3735(19) no
N1 H1N . . 0.88(2) no
N2 H2N . . 0.899(19) no
C1 C9 . . 1.5224(18) no
C1 C2 . . 1.375(2) no
C2 C3 . . 1.427(2) no
C3 C4 . . 1.364(2) no
C5 C6 . . 1.374(2) no
C5 C9 . . 1.512(2) no
C6 C7 . . 1.416(3) no
C7 C8 . . 1.368(3) no
C9 C10 . . 1.544(2) no
C9 C13 . . 1.538(2) no
C10 C11 . . 1.530(2) no
C11 C12 . . 1.504(2) no
C2 H2 . . 0.9500 no
C3 H3 . . 0.9500 no
C4 H4 . . 0.9500 no
C6 H6 . . 0.9500 no
C7 H7 . . 0.9500 no
C8 H8 . . 0.9500 no
C10 H10A . . 0.9900 no
C10 H10B . . 0.9900 no
C11 H11A . . 0.9900 no
C11 H11B . . 0.9900 no
C12 H12A . . 0.9900 no
C12 H12B . . 0.9900 no
C13 H13A . . 0.9800 no
C13 H13B . . 0.9800 no
C13 H13C . . 0.9800 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 1_545 0.88(2) 2.05(2) 2.9238(18) 174.3(19) yes
N2 H2N O1 2_647 0.90(2) 2.06(2) 2.9529(18) 171.5(19) yes
O1 H1O Cg1 1_565 0.87(3) 2.53 3.20 135 yes
O1 H1O Cg2 1_565 0.87(3) 2.64 3.10 114 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C2 . . . . -1.41(16) no
C4 N1 C1 C9 . . . . -179.27(12) no
C1 N1 C4 C3 . . . . 1.08(17) no
C8 N2 C5 C6 . . . . -0.4(2) no
C8 N2 C5 C9 . . . . 178.81(15) no
C5 N2 C8 C7 . . . . 0.5(2) no
N1 C1 C2 C3 . . . . 1.17(17) no
C9 C1 C2 C3 . . . . 178.74(14) no
N1 C1 C9 C5 . . . . -32.86(18) no
N1 C1 C9 C10 . . . . -155.52(13) no
N1 C1 C9 C13 . . . . 86.97(15) no
C2 C1 C9 C5 . . . . 149.85(15) no
C2 C1 C9 C10 . . . . 27.2(2) no
C2 C1 C9 C13 . . . . -90.32(18) no
C1 C2 C3 C4 . . . . -0.53(18) no
C2 C3 C4 N1 . . . . -0.33(17) no
N2 C5 C6 C7 . . . . 0.2(2) no
C9 C5 C6 C7 . . . . -178.96(17) no
N2 C5 C9 C1 . . . . -45.13(18) no
N2 C5 C9 C10 . . . . 76.94(16) no
N2 C5 C9 C13 . . . . -164.83(14) no
C6 C5 C9 C1 . . . . 133.92(18) no
C6 C5 C9 C10 . . . . -104.0(2) no
C6 C5 C9 C13 . . . . 14.2(2) no
C5 C6 C7 C8 . . . . 0.1(2) no
C6 C7 C8 N2 . . . . -0.4(3) no
C1 C9 C10 C11 . . . . 61.87(15) no
C5 C9 C10 C11 . . . . -60.36(15) no
C13 C9 C10 C11 . . . . -179.65(12) no
C9 C10 C11 C12 . . . . -166.90(12) no
C10 C11 C12 O1 . . . . 173.65(12) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744155
