#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/50/2225027.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_2225027
loop_
_publ_author_name
'Journot, Guillaume'
'Neier, Reinhard'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 2,2'-(Propane-2,2-diyl)bis(1H-pyrrole)
;
_journal_coeditor_code           IS2506
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o392
_journal_paper_doi               10.1107/S1600536809054701
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H14 N2'
_chemical_formula_moiety         'C11 H14 N2'
_chemical_formula_sum            'C11 H14 N2'
_chemical_formula_weight         174.24
_chemical_name_common            meso-Dimethylbis(pyrrol-2-yl)methane
_chemical_name_systematic
;
2,2'-(propane-2,2-diyl)bis(1H-pyrrole)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.802(7)
_cell_angle_beta                 95.321(7)
_cell_angle_gamma                97.328(7)
_cell_formula_units_Z            4
_cell_length_a                   8.4554(8)
_cell_length_b                   9.2001(8)
_cell_length_c                   13.2274(11)
_cell_measurement_reflns_used    10442
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.53
_cell_measurement_theta_min      1.57
_cell_volume                     998.74(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'φ and 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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15270
_diffrn_reflns_theta_full        29.18
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0448
_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)+(0.0549P)²+0.0012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                3816
_reflns_number_total             5385
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2506.cif
_cod_data_source_block           I
_cod_original_cell_volume        998.74(15)
_cod_database_code               2225027
_cod_database_fobs_code          2225027
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-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
N N1 0.12135(12) 0.25140(11) 0.31284(8) 0.0249(3) Uani . . 1.000
N N2 0.40689(12) 0.01811(11) 0.24234(8) 0.0252(3) Uani . . 1.000
C C1 0.13663(14) 0.38021(14) 0.38492(10) 0.0312(4) Uani . . 1.000
C C2 0.17507(15) 0.34619(16) 0.47962(10) 0.0348(4) Uani . . 1.000
C C3 0.18351(15) 0.19174(16) 0.46471(9) 0.0311(4) Uani . . 1.000
C C4 0.14934(13) 0.13454(13) 0.36055(9) 0.0234(3) Uani . . 1.000
C C5 0.24635(14) -0.03734(12) 0.22005(9) 0.0226(3) Uani . . 1.000
C C6 0.22365(16) -0.10944(14) 0.11865(9) 0.0305(4) Uani . . 1.000
C C7 0.37369(18) -0.09563(15) 0.07953(10) 0.0358(4) Uani . . 1.000
C C8 0.48462(16) -0.01599(14) 0.15732(10) 0.0314(4) Uani . . 1.000
C C9 0.13255(15) -0.02364(14) 0.30167(9) 0.0277(3) Uani . . 1.000
C C10 -0.04155(17) -0.07156(17) 0.24923(13) 0.0470(5) Uani . . 1.000
C C11 0.1699(2) -0.12827(17) 0.37732(13) 0.0479(5) Uani . . 1.000
N N21 0.51399(12) 0.37264(11) 0.36601(7) 0.0232(3) Uani . . 1.000
N N22 0.32603(13) 0.28069(11) 0.11006(7) 0.0253(3) Uani . . 1.000
C C21 0.59997(14) 0.28840(14) 0.42014(9) 0.0264(3) Uani . . 1.000
C C22 0.73108(15) 0.26137(15) 0.37047(10) 0.0308(4) Uani . . 1.000
C C23 0.72320(14) 0.33192(14) 0.28313(9) 0.0281(4) Uani . . 1.000
C C24 0.58798(13) 0.40056(13) 0.28184(8) 0.0225(3) Uani . . 1.000
C C25 0.35755(14) 0.42785(13) 0.15697(8) 0.0229(3) Uani . . 1.000
C C26 0.21946(16) 0.48825(14) 0.13876(9) 0.0298(4) Uani . . 1.000
C C27 0.10133(16) 0.37382(15) 0.07998(10) 0.0340(4) Uani . . 1.000
C C28 0.17016(15) 0.24721(14) 0.06366(9) 0.0307(3) Uani . . 1.000
C C29 0.52308(14) 0.49773(13) 0.21071(9) 0.0251(3) Uani . . 1.000
C C30 0.51173(19) 0.65164(14) 0.27414(11) 0.0381(4) Uani . . 1.000
C C31 0.63878(17) 0.51784(17) 0.12898(10) 0.0381(4) Uani . . 1.000
H H1N 0.1032(19) 0.2477(18) 0.2475(13) 0.040(4) Uiso . . 1.000
H H2N 0.4531(19) 0.0726(18) 0.2990(12) 0.040(4) Uiso . . 1.000
H H1 0.12280 0.47620 0.37120 0.0370 Uiso calc R 1.000
H H2 0.19290 0.41380 0.54380 0.0420 Uiso calc R 1.000
H H3 0.20840 0.13690 0.51730 0.0370 Uiso calc R 1.000
H H6 0.12470 -0.15960 0.08150 0.0370 Uiso calc R 1.000
H H7 0.39370 -0.13470 0.01140 0.0430 Uiso calc R 1.000
H H8 0.59580 0.01080 0.15310 0.0380 Uiso calc R 1.000
H H10A -0.11590 -0.06340 0.30180 0.0710 Uiso calc R 1.000
H H10B -0.05400 -0.17510 0.21260 0.0710 Uiso calc R 1.000
H H10C -0.06530 -0.00660 0.20000 0.0710 Uiso calc R 1.000
H H11A 0.09550 -0.12180 0.43000 0.0720 Uiso calc R 1.000
H H11B 0.28040 -0.09850 0.41070 0.0720 Uiso calc R 1.000
H H11C 0.15750 -0.23100 0.33940 0.0720 Uiso calc R 1.000
H H21N 0.4231(19) 0.4002(16) 0.3827(11) 0.031(4) Uiso . . 1.000
H H22N 0.3894(19) 0.2146(18) 0.1123(11) 0.039(4) Uiso . . 1.000
H H21 0.57330 0.25470 0.48130 0.0320 Uiso calc R 1.000
H H22 0.81210 0.20590 0.39070 0.0370 Uiso calc R 1.000
H H23 0.79840 0.33180 0.23400 0.0340 Uiso calc R 1.000
H H26 0.20540 0.58890 0.16150 0.0360 Uiso calc R 1.000
H H27 -0.00570 0.38380 0.05650 0.0410 Uiso calc R 1.000
H H28 0.11950 0.15250 0.02670 0.0370 Uiso calc R 1.000
H H30A 0.47170 0.71520 0.22810 0.0570 Uiso calc R 1.000
H H30B 0.61830 0.69770 0.30870 0.0570 Uiso calc R 1.000
H H30C 0.43790 0.64010 0.32610 0.0570 Uiso calc R 1.000
H H31A 0.64370 0.42070 0.08640 0.0570 Uiso calc R 1.000
H H31B 0.74620 0.56090 0.16360 0.0570 Uiso calc R 1.000
H H31C 0.60000 0.58470 0.08510 0.0570 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C4 . . . 109.93(10) no
C5 N2 C8 . . . 110.24(10) no
C1 N1 H1N . . . 123.9(11) no
C4 N1 H1N . . . 126.1(11) no
C5 N2 H2N . . . 126.5(11) no
C8 N2 H2N . . . 123.1(11) no
C21 N21 C24 . . . 110.16(10) no
C25 N22 C28 . . . 110.04(10) no
C21 N21 H21N . . . 123.5(9) no
C24 N21 H21N . . . 126.3(9) no
C28 N22 H22N . . . 123.0(11) no
C25 N22 H22N . . . 126.8(11) no
N1 C1 C2 . . . 107.93(12) no
C1 C2 C3 . . . 107.31(12) no
C2 C3 C4 . . . 108.08(11) no
C3 C4 C9 . . . 130.99(12) no
N1 C4 C9 . . . 122.17(10) no
N1 C4 C3 . . . 106.75(11) no
N2 C5 C6 . . . 106.70(11) no
C6 C5 C9 . . . 131.40(11) no
N2 C5 C9 . . . 121.74(10) no
C5 C6 C7 . . . 107.85(11) no
C6 C7 C8 . . . 107.59(12) no
N2 C8 C7 . . . 107.61(12) no
C4 C9 C5 . . . 111.44(10) no
C10 C9 C11 . . . 109.12(12) no
C5 C9 C10 . . . 109.09(10) no
C5 C9 C11 . . . 108.66(11) no
C4 C9 C10 . . . 109.10(11) no
C4 C9 C11 . . . 109.41(10) no
N1 C1 H1 . . . 126.00 no
C2 C1 H1 . . . 126.00 no
C3 C2 H2 . . . 126.00 no
C1 C2 H2 . . . 126.00 no
C4 C3 H3 . . . 126.00 no
C2 C3 H3 . . . 126.00 no
C7 C6 H6 . . . 126.00 no
C5 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 . . . 109.00 no
C9 C10 H10B . . . 109.00 no
C9 C10 H10C . . . 109.00 no
H10B C10 H10C . . . 110.00 no
H10A C10 H10C . . . 109.00 no
H10A C10 H10B . . . 109.00 no
C9 C11 H11C . . . 109.00 no
H11A C11 H11B . . . 109.00 no
H11A C11 H11C . . . 109.00 no
H11B C11 H11C . . . 109.00 no
C9 C11 H11B . . . 109.00 no
C9 C11 H11A . . . 109.00 no
N21 C21 C22 . . . 107.86(11) no
C21 C22 C23 . . . 107.02(11) no
C22 C23 C24 . . . 108.20(11) no
C23 C24 C29 . . . 131.63(10) no
N21 C24 C23 . . . 106.75(10) no
N21 C24 C29 . . . 121.55(10) no
N22 C25 C29 . . . 121.59(11) no
C26 C25 C29 . . . 131.53(11) no
N22 C25 C26 . . . 106.79(10) no
C25 C26 C27 . . . 108.09(11) no
C26 C27 C28 . . . 107.19(12) no
N22 C28 C27 . . . 107.89(11) no
C25 C29 C31 . . . 109.40(10) no
C30 C29 C31 . . . 108.82(11) no
C25 C29 C30 . . . 109.04(10) no
C24 C29 C25 . . . 110.94(10) no
C24 C29 C30 . . . 109.35(10) no
C24 C29 C31 . . . 109.26(10) no
N21 C21 H21 . . . 126.00 no
C22 C21 H21 . . . 126.00 no
C21 C22 H22 . . . 126.00 no
C23 C22 H22 . . . 127.00 no
C22 C23 H23 . . . 126.00 no
C24 C23 H23 . . . 126.00 no
C25 C26 H26 . . . 126.00 no
C27 C26 H26 . . . 126.00 no
C26 C27 H27 . . . 126.00 no
C28 C27 H27 . . . 126.00 no
N22 C28 H28 . . . 126.00 no
C27 C28 H28 . . . 126.00 no
C29 C30 H30A . . . 109.00 no
C29 C30 H30B . . . 109.00 no
C29 C30 H30C . . . 109.00 no
H30A C30 H30B . . . 110.00 no
H30A C30 H30C . . . 109.00 no
H30B C30 H30C . . . 109.00 no
C29 C31 H31A . . . 109.00 no
C29 C31 H31B . . . 109.00 no
C29 C31 H31C . . . 109.00 no
H31A C31 H31B . . . 109.00 no
H31A C31 H31C . . . 110.00 no
H31B C31 H31C . . . 109.00 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
N1 C1 . . 1.3724(17) no
N1 C4 . . 1.3705(16) no
N2 C5 . . 1.3739(16) no
N2 C8 . . 1.3655(17) no
N1 H1N . . 0.858(17) no
N2 H2N . . 0.856(16) no
N21 C21 . . 1.3704(16) no
N21 C24 . . 1.3720(14) no
N22 C25 . . 1.3712(15) no
N22 C28 . . 1.3750(17) no
N21 H21N . . 0.875(16) no
N22 H22N . . 0.863(16) no
C1 C2 . . 1.3626(19) no
C2 C3 . . 1.413(2) no
C3 C4 . . 1.3781(17) no
C4 C9 . . 1.5118(17) no
C5 C6 . . 1.3757(17) no
C5 C9 . . 1.5115(17) no
C6 C7 . . 1.413(2) no
C7 C8 . . 1.3654(19) no
C9 C11 . . 1.541(2) no
C9 C10 . . 1.544(2) no
C1 H1 . . 0.9500 no
C2 H2 . . 0.9500 no
C3 H3 . . 0.9500 no
C6 H6 . . 0.9500 no
C7 H7 . . 0.9500 no
C8 H8 . . 0.9500 no
C10 H10C . . 0.9800 no
C10 H10B . . 0.9800 no
C10 H10A . . 0.9800 no
C11 H11B . . 0.9800 no
C11 H11A . . 0.9800 no
C11 H11C . . 0.9800 no
C21 C22 . . 1.3683(18) no
C22 C23 . . 1.4186(18) no
C23 C24 . . 1.3750(17) no
C24 C29 . . 1.5170(16) no
C25 C29 . . 1.5192(17) no
C25 C26 . . 1.3744(18) no
C26 C27 . . 1.4211(19) no
C27 C28 . . 1.3612(19) no
C29 C31 . . 1.5421(18) no
C29 C30 . . 1.5373(18) no
C21 H21 . . 0.9500 no
C22 H22 . . 0.9500 no
C23 H23 . . 0.9500 no
C26 H26 . . 0.9500 no
C27 H27 . . 0.9500 no
C28 H28 . . 0.9500 no
C30 H30A . . 0.9800 no
C30 H30B . . 0.9800 no
C30 H30C . . 0.9800 no
C31 H31A . . 0.9800 no
C31 H31B . . 0.9800 no
C31 H31C . . 0.9800 no
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 . . . . 0.14(14) no
C1 N1 C4 C3 . . . . -0.25(13) no
C1 N1 C4 C9 . . . . 176.69(11) no
C8 N2 C5 C6 . . . . 0.67(14) no
C8 N2 C5 C9 . . . . 176.51(11) no
C5 N2 C8 C7 . . . . -0.63(14) no
C21 N21 C24 C29 . . . . -177.09(10) no
C24 N21 C21 C22 . . . . -0.03(13) no
C21 N21 C24 C23 . . . . 0.15(13) no
C28 N22 C25 C26 . . . . -0.63(13) no
C28 N22 C25 C29 . . . . -177.43(10) no
C25 N22 C28 C27 . . . . 0.54(14) no
N1 C1 C2 C3 . . . . 0.02(14) no
C1 C2 C3 C4 . . . . -0.17(15) no
C2 C3 C4 C9 . . . . -176.31(12) no
C2 C3 C4 N1 . . . . 0.25(14) no
N1 C4 C9 C5 . . . . 60.57(15) no
N1 C4 C9 C11 . . . . -179.26(11) no
C3 C4 C9 C5 . . . . -123.33(14) no
N1 C4 C9 C10 . . . . -59.95(15) no
C3 C4 C9 C11 . . . . -3.15(19) no
C3 C4 C9 C10 . . . . 116.16(15) no
N2 C5 C9 C4 . . . . 49.85(15) no
C9 C5 C6 C7 . . . . -175.73(12) no
N2 C5 C6 C7 . . . . -0.44(14) no
C6 C5 C9 C4 . . . . -135.46(13) no
N2 C5 C9 C10 . . . . 170.37(11) no
N2 C5 C9 C11 . . . . -70.77(14) no
C6 C5 C9 C10 . . . . -14.94(19) no
C6 C5 C9 C11 . . . . 103.92(15) no
C5 C6 C7 C8 . . . . 0.07(16) no
C6 C7 C8 N2 . . . . 0.34(15) no
N21 C21 C22 C23 . . . . -0.10(15) no
C21 C22 C23 C24 . . . . 0.19(15) no
C22 C23 C24 N21 . . . . -0.21(14) no
C22 C23 C24 C29 . . . . 176.64(12) no
N21 C24 C29 C25 . . . . -63.67(14) no
N21 C24 C29 C30 . . . . 56.63(15) no
N21 C24 C29 C31 . . . . 175.64(11) no
C23 C24 C29 C25 . . . . 119.88(14) no
C23 C24 C29 C30 . . . . -119.82(14) no
C23 C24 C29 C31 . . . . -0.82(18) no
N22 C25 C26 C27 . . . . 0.48(13) no
C29 C25 C26 C27 . . . . 176.83(12) no
N22 C25 C29 C24 . . . . -47.82(14) no
N22 C25 C29 C30 . . . . -168.30(10) no
N22 C25 C29 C31 . . . . 72.79(14) no
C26 C25 C29 C24 . . . . 136.28(13) no
C26 C25 C29 C30 . . . . 15.80(17) no
C26 C25 C29 C31 . . . . -103.11(15) no
C25 C26 C27 C28 . . . . -0.16(14) no
C26 C27 C28 N22 . . . . -0.23(14) no
