#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:52:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178409 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/30/4023072.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_4023072
loop_
_publ_author_name
'Sanjeev K. Dey'
'David A. Lightner'
_publ_section_title
;
 1,1'-Bipyrroles: Synthesis and Stereochemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9395
_journal_page_last               9397
_journal_paper_doi               10.1021/jo7016789
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C8 H8 N2'
_chemical_formula_weight         132.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7984(2)
_cell_length_b                   10.7984(2)
_cell_length_c                   11.9281(2)
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.45
_cell_measurement_theta_min      2.54
_cell_volume                     1390.88(4)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6312
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0352
_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)+(0.0742P)²+0.6478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                582
_reflns_number_total             617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7016789-File001.cif
_cod_data_source_block           skd2131
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               4023072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
N1 N 0.56255(9) 0.26382(8) 0.04140(8) 0.0200(4) Uani 1 1 d .
C5 C 0.61629(11) 0.35756(10) -0.01993(9) 0.0216(4) Uani 1 1 d .
H5A H 0.5748 0.4146 -0.0675 0.026 Uiso 1 1 calc R
C4 C 0.74056(11) 0.35289(11) 0.00054(9) 0.0233(4) Uani 1 1 d .
H4A H 0.8016 0.4066 -0.0300 0.028 Uiso 1 1 calc R
C2 C 0.65088(11) 0.19967(11) 0.09997(10) 0.0231(4) Uani 1 1 d .
H2A H 0.6373 0.1310 0.1482 0.028 Uiso 1 1 calc R
C3 C 0.76207(11) 0.25330(11) 0.07570(10) 0.0249(4) Uani 1 1 d .
H3A H 0.8403 0.2283 0.1042 0.030 Uiso 1 1 calc R
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
N1 0.0193(6) 0.0201(6) 0.0207(6) 0.0002(4) 0.0002(4) -0.0023(3)
C5 0.0271(7) 0.0196(6) 0.0181(6) 0.0002(4) 0.0008(4) -0.0039(4)
C4 0.0241(7) 0.0238(7) 0.0218(7) -0.0034(4) 0.0046(4) -0.0057(5)
C2 0.0253(7) 0.0194(6) 0.0248(7) 0.0011(4) -0.0014(4) 0.0008(4)
C3 0.0206(6) 0.0246(6) 0.0294(7) -0.0031(5) -0.0002(5) 0.0027(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C2 N1 C5 110.43(10) .
C2 N1 N1 124.79(10) 6_554
C5 N1 N1 124.76(10) 6_554
C4 C5 N1 106.99(10) .
C4 C5 H5A 126.5 .
N1 C5 H5A 126.5 .
C5 C4 C3 107.57(10) .
C5 C4 H4A 126.2 .
C3 C4 H4A 126.2 .
C3 C2 N1 106.85(10) .
C3 C2 H2A 126.6 .
N1 C2 H2A 126.6 .
C2 C3 C4 108.16(11) .
C2 C3 H3A 125.9 .
C4 C3 H3A 125.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.3703(15) .
N1 C5 1.3772(15) .
N1 N1 1.3834(18) 6_554
C5 C4 1.3648(17) .
C5 H5A 0.9500 .
C4 C3 1.4193(18) .
C4 H4A 0.9500 .
C2 C3 1.3641(17) .
C2 H2A 0.9500 .
C3 H3A 0.9500 .
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
_geom_torsion_site_symmetry_1
C2 N1 C5 C4 -0.23(12) .
N1 N1 C5 C4 -178.56(9) 6_554
N1 C5 C4 C3 0.30(12) .
C5 N1 C2 C3 0.06(12) .
N1 N1 C2 C3 178.39(9) 6_554
N1 C2 C3 C4 0.13(13) .
C5 C4 C3 C2 -0.27(14) .
