#------------------------------------------------------------------------------
#$Date: 2019-12-27 22:23:32 +0200 (Fri, 27 Dec 2019) $
#$Revision: 246250 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312021.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_2312021
loop_
_publ_author_name
'Michaels, Christopher A.'
'Zakharov, Lev N.'
'Lamm, Ashley N.'
_publ_section_title
;
 Crystal structure of 2,2'-bi-pyrrole.
;
_journal_coeditor_code           HB7692
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1517
_journal_page_last               1519
_journal_paper_doi               10.1107/S2056989017013433
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H8 N2'
_chemical_formula_moiety         'C8 H8 N2'
_chemical_formula_sum            'C8 H8 N2'
_chemical_formula_weight         132.16
_chemical_name_systematic
;
2,2'-Bipyrrole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.746(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9500(2)
_cell_length_b                   6.7650(2)
_cell_length_c                   8.4363(3)
_cell_measurement_reflns_used    1086
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.45
_cell_measurement_theta_min      7.50
_cell_volume                     337.225(19)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHEXLTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1989
_diffrn_reflns_theta_full        66.531
_diffrn_reflns_theta_max         66.531
_diffrn_reflns_theta_min         7.496
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             140
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0657P)²+0.0340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                540
_reflns_number_total             590
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7692sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        337.224(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312021
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
N N1 0.53346(18) 1.09945(15) 0.20670(12) 0.0322(4) Uani d 1
C C1 0.7071(2) 1.07425(18) 0.32546(15) 0.0352(4) Uani d 1
C C2 0.8665(2) 0.95786(18) 0.26832(16) 0.0330(4) Uani d 1
C C3 0.7857(2) 0.91019(17) 0.10841(15) 0.0297(4) Uani d 1
C C4 0.57828(19) 0.99966(16) 0.07196(13) 0.0263(4) Uani d 1
H H1 0.704(2) 1.135(2) 0.4292(17) 0.043(4) Uiso d 1
H H1N 0.407(2) 1.170(3) 0.2168(17) 0.046(4) Uiso d 1
H H2 1.010(3) 0.916(2) 0.3269(19) 0.041(4) Uiso d 1
H H3 0.859(2) 0.831(2) 0.0354(16) 0.039(4) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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_3
_geom_angle
C1 N1 C4 . 110.02(11)
C1 N1 H1N . 124.3(9)
C4 N1 H1N . 125.6(9)
N1 C1 C2 . 108.12(11)
N1 C1 H1 . 121.2(9)
C2 C1 H1 . 130.7(9)
C1 C2 C3 . 107.23(11)
C1 C2 H2 . 126.4(9)
C3 C2 H2 . 126.4(9)
C4 C3 C2 . 107.93(11)
C4 C3 H3 . 124.4(8)
C2 C3 H3 . 127.6(8)
N1 C4 C3 . 106.69(11)
N1 C4 C4 3_675 121.74(13)
C3 C4 C4 3_675 131.57(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.3628(18)
N1 C4 . 1.3748(15)
N1 H1N . 0.907(16)
C1 C2 . 1.3635(19)
C1 H1 . 0.970(15)
C2 C3 . 1.4151(19)
C2 H2 . 0.979(16)
C3 C4 . 1.3767(17)
C3 H3 . 0.959(14)
C4 C4 3_675 1.441(2)
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_655 0.907(16) 2.499(19) 3.2275(12) 138.1(13)
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_4
_geom_torsion
C4 N1 C1 C2 . 0.11(14)
N1 C1 C2 C3 . -0.15(14)
C1 C2 C3 C4 . 0.13(14)
C1 N1 C4 C3 . -0.03(13)
C1 N1 C4 C4 3_675 179.68(12)
C2 C3 C4 N1 . -0.07(13)
C2 C3 C4 C4 3_675 -179.73(15)

_cod_database_fobs_code 2312021
