#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238806.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_2238806
loop_
_publ_author_name
'Kim, Chong-Hyeak'
'Jeon, Yea-Sel'
'Lynch, Vincent'
'Sessler, Jonathan L.'
'Hwang, Kwang-Jin'
_publ_section_title
;
 2-[(1H-Pyrrol-2-yl)methyl]-1H-pyrrole
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1697
_journal_paper_doi               10.1107/S1600536813028365
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C9 H10 N2'
_chemical_formula_moiety         'C9 H10 N2'
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.19
_chemical_name_systematic
;
2-[(1H-Pyrrol-2-yl)methyl]-1H-pyrrole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.048(3)
_cell_length_b                   7.312(4)
_cell_length_c                   9.024(5)
_cell_measurement_reflns_used    4189
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     392.0(4)
_computing_cell_refinement
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2008)
;
_computing_data_collection
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2008)
;
_computing_data_reduction
;
CrystalClear (Molecular Structure Corporation & Rigaku, 2008)
;
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury 2 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     0.71075
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4179
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.227
_refine_ls_abs_structure_details nd
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1786
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0567
_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)+(0.0490P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                1374
_reflns_number_total             1786
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5264.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2238806
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.2619(4) -0.0035(4) 0.5615(3) 0.0353(6) Uani d . 1 1
H H1 0.3300 -0.0409 0.6603 0.042 Uiso calc R 1 1
C C2 0.3488(4) 0.1182(4) 0.4732(3) 0.0331(6) Uani d U 1 1
H H2 0.4887 0.1802 0.4991 0.040 Uiso calc R 1 1
C C3 0.1930(4) 0.1352(3) 0.3367(3) 0.0298(6) Uani d U 1 1
H H3 0.2088 0.2109 0.2538 0.036 Uiso calc R 1 1
C C4 0.0136(4) 0.0222(4) 0.3451(2) 0.0284(5) Uani d U 1 1
C C5 -0.2014(4) -0.0146(4) 0.2387(2) 0.0348(6) Uani d U 1 1
H H5A -0.3267 0.0374 0.2818 0.042 Uiso calc R 1 1
H H5B -0.2242 -0.1486 0.2310 0.042 Uiso calc R 1 1
C C6 -0.2144(4) 0.0606(3) 0.0837(3) 0.0301(6) Uani d U 1 1
C C7 -0.3568(4) 0.1863(4) 0.0037(3) 0.0342(6) Uani d U 1 1
H H7 -0.4721 0.2516 0.0396 0.041 Uiso calc R 1 1
C C8 -0.3029(4) 0.2019(4) -0.1402(3) 0.0362(6) Uani d U 1 1
H H8 -0.3761 0.2785 -0.2195 0.043 Uiso calc R 1 1
C C9 -0.1268(4) 0.0876(4) -0.1462(2) 0.0367(6) Uani d U 1 1
H H9 -0.0530 0.0711 -0.2294 0.044 Uiso calc R 1 1
N N1 0.0597(4) -0.0620(3) 0.4825(2) 0.0344(6) Uani d U 1 1
H H1N -0.0283 -0.1423 0.5153 0.041 Uiso calc R 1 1
N N2 -0.0764(3) 0.0011(3) -0.0094(2) 0.0336(5) Uani d U 1 1
H H2N 0.0302 -0.0813 0.0148 0.040 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0380(14) 0.0427(15) 0.0244(12) 0.0079(13) 0.0037(11) -0.0002(12)
C2 0.0322(13) 0.0322(14) 0.0356(13) -0.0001(11) 0.0082(11) -0.0078(11)
C3 0.0366(13) 0.0265(13) 0.0292(12) -0.0002(10) 0.0135(11) 0.0000(10)
C4 0.0349(12) 0.0269(13) 0.0249(11) 0.0027(10) 0.0096(10) 0.0001(9)
C5 0.0311(12) 0.0358(14) 0.0388(14) -0.0030(11) 0.0103(11) 0.0009(11)
C6 0.0281(12) 0.0290(14) 0.0322(13) -0.0035(10) 0.0030(10) -0.0048(10)
C7 0.0248(13) 0.0328(14) 0.0438(15) 0.0010(11) 0.0031(11) 0.0001(11)
C8 0.0343(14) 0.0296(14) 0.0394(14) -0.0002(11) -0.0070(12) 0.0034(11)
C9 0.0459(14) 0.0375(16) 0.0248(13) -0.0032(13) 0.0016(11) -0.0026(11)
N1 0.0388(12) 0.0334(13) 0.0323(11) -0.0030(10) 0.0100(10) 0.0038(9)
N2 0.0371(11) 0.0287(11) 0.0345(11) 0.0064(10) 0.0058(9) 0.0006(9)
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 C1 N1 107.8(2)
C2 C1 H1 126.1
N1 C1 H1 126.1
C1 C2 C3 107.5(2)
C1 C2 H2 126.3
C3 C2 H2 126.3
C4 C3 C2 107.7(2)
C4 C3 H3 126.2
C2 C3 H3 126.2
N1 C4 C3 107.0(2)
N1 C4 C5 120.6(2)
C3 C4 C5 132.4(2)
C4 C5 C6 115.1(2)
C4 C5 H5A 108.5
C6 C5 H5A 108.5
C4 C5 H5B 108.5
C6 C5 H5B 108.5
H5A C5 H5B 107.5
N2 C6 C7 106.7(2)
N2 C6 C5 122.0(2)
C7 C6 C5 131.2(2)
C6 C7 C8 108.1(2)
C6 C7 H7 125.9
C8 C7 H7 125.9
C9 C8 C7 107.8(2)
C9 C8 H8 126.1
C7 C8 H8 126.1
C8 C9 N2 107.0(2)
C8 C9 H9 126.5
N2 C9 H9 126.5
C1 N1 C4 110.1(2)
C1 N1 H1N 124.9
C4 N1 H1N 124.9
C6 N2 C9 110.5(2)
C6 N2 H2N 124.8
C9 N2 H2N 124.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.363(4)
C1 N1 1.364(3)
C1 H1 0.9500
C2 C3 1.410(3)
C2 H2 0.9500
C3 C4 1.377(3)
C3 H3 0.9500
C4 N1 1.365(3)
C4 C5 1.490(3)
C5 C6 1.491(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 N2 1.361(3)
C6 C7 1.370(3)
C7 C8 1.402(3)
C7 H7 0.9500
C8 C9 1.363(3)
C8 H8 0.9500
C9 N2 1.369(3)
C9 H9 0.9500
N1 H1N 0.8800
N2 H2N 0.8800
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
N1 H1N Cg1 2_546 0.88 2.53 3.357(3) 156
N2 H2N Cg2 2_545 0.88 2.53 3.363(3) 159
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
N1 C1 C2 C3 0.5(3)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 N1 -0.4(3)
C2 C3 C4 C5 178.4(3)
N1 C4 C5 C6 -170.1(2)
C3 C4 C5 C6 11.2(4)
C4 C5 C6 N2 64.4(3)
C4 C5 C6 C7 -118.6(3)
N2 C6 C7 C8 0.1(3)
C5 C6 C7 C8 -177.2(2)
C6 C7 C8 C9 -0.7(3)
C7 C8 C9 N2 1.1(3)
C2 C1 N1 C4 -0.8(3)
C3 C4 N1 C1 0.7(3)
C5 C4 N1 C1 -178.3(2)
C7 C6 N2 C9 0.6(3)
C5 C6 N2 C9 178.2(2)
C8 C9 N2 C6 -1.0(3)
