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#$Date: 2016-03-26 15:46:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180315 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152935.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_7152935
loop_
_publ_author_name
'Kaschel, Johannes'
'Schneider, Tobias F.'
'Kratzert, Daniel'
'Stalke, Dietmar'
'Werz, Daniel B.'
_publ_section_title
;
 Symmetric and unsymmetric 3,3'-linked bispyrroles via ring-enlargement
 reactions of furan-derived donor-acceptor cyclopropanes.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3494
_journal_page_last               3509
_journal_paper_doi               10.1039/c3ob40228b
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C26 H21 N O2'
_chemical_formula_sum            'C26 H21 N O2'
_chemical_formula_weight         379.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 93.106(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.313(3)
_cell_length_b                   12.727(2)
_cell_length_c                   8.9581(15)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      135.561
_cell_measurement_theta_min      8.626
_cell_volume                     1971.0(6)
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_collection       'APEX2 v2010.7'
_computing_data_reduction        'SAINT V7.68A'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker Smart-6000'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'INCOATEC mirror optics'
_diffrn_radiation_source         'Bruker SMART-Cu rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16522
_diffrn_reflns_theta_full        68.37
_diffrn_reflns_theta_max         68.37
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.8777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/2
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0297
_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)+(0.0344P)²+1.1568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                1638
_reflns_number_total             1777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40228b.txt
_cod_data_source_block           JKDX09B
_cod_original_cell_volume        1970.9(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7152935
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.0000 1.12193(10) 0.2500 0.0224(3) Uani 1 2 d S
O1 O 0.13855(4) 0.83988(6) 0.16084(8) 0.0306(2) Uani 1 1 d .
C1 C 0.0000 1.45251(14) 0.2500 0.0419(4) Uani 1 2 d S
H1 H 0.0000 1.5271 0.2500 0.050 Uiso 1 2 calc SR
C2 C -0.05031(7) 1.39768(10) 0.15389(15) 0.0388(3) Uani 1 1 d .
H2 H -0.0848 1.4351 0.0870 0.047 Uiso 1 1 calc R
C3 C -0.05120(7) 1.28873(9) 0.15376(13) 0.0306(3) Uani 1 1 d .
H3 H -0.0867 1.2519 0.0882 0.037 Uiso 1 1 calc R
C4 C 0.0000 1.23338(12) 0.2500 0.0250(3) Uani 1 2 d S
C5 C 0.04556(6) 1.05782(8) 0.34359(11) 0.0228(2) Uani 1 1 d .
H5 H 0.0821 1.0812 0.4192 0.027 Uiso 1 1 calc R
C6 C 0.02924(6) 0.95574(8) 0.30921(11) 0.0222(2) Uani 1 1 d .
C7 C 0.06667(6) 0.86116(8) 0.38049(11) 0.0234(2) Uani 1 1 d .
H7A H 0.0260 0.8096 0.4021 0.028 Uiso 1 1 calc R
H7B H 0.0926 0.8822 0.4771 0.028 Uiso 1 1 calc R
C8 C 0.12588(6) 0.80786(8) 0.28560(11) 0.0234(2) Uani 1 1 d .
C9 C 0.16800(6) 0.71425(8) 0.34924(11) 0.0228(2) Uani 1 1 d .
C10 C 0.15011(6) 0.66920(9) 0.48499(12) 0.0266(3) Uani 1 1 d .
H10 H 0.1101 0.6985 0.5403 0.032 Uiso 1 1 calc R
C11 C 0.19025(6) 0.58198(9) 0.53988(13) 0.0297(3) Uani 1 1 d .
H11 H 0.1777 0.5517 0.6324 0.036 Uiso 1 1 calc R
C12 C 0.24875(6) 0.53896(9) 0.45978(12) 0.0291(3) Uani 1 1 d .
H12 H 0.2758 0.4786 0.4967 0.035 Uiso 1 1 calc R
C13 C 0.26791(6) 0.58387(9) 0.32592(12) 0.0298(3) Uani 1 1 d .
H13 H 0.3086 0.5549 0.2721 0.036 Uiso 1 1 calc R
C14 C 0.22791(6) 0.67068(9) 0.27053(12) 0.0277(3) Uani 1 1 d .
H14 H 0.2412 0.7010 0.1784 0.033 Uiso 1 1 calc R
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'
O O 0.0492 0.0322 '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_1
_geom_angle_site_symmetry_3
C5 N1 C5 107.83(12) 2 .
C5 N1 C4 126.08(6) 2 .
C5 N1 C4 126.08(6) . .
C2 C1 C2 119.27(16) . 2
C2 C1 H1 120.4 . .
C2 C1 H1 120.4 2 .
C1 C2 C3 120.84(12) . .
C1 C2 H2 119.6 . .
C3 C2 H2 119.6 . .
C2 C3 C4 119.88(12) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C3 C4 C3 119.28(15) . 2
C3 C4 N1 120.36(7) . .
C3 C4 N1 120.36(7) 2 .
C6 C5 N1 108.71(9) . .
C6 C5 H5 125.6 . .
N1 C5 H5 125.6 . .
C5 C6 C6 107.37(6) . 2
C5 C6 C7 126.33(9) . .
C6 C6 C7 126.29(6) 2 .
C6 C7 C8 114.15(9) . .
C6 C7 H7A 108.7 . .
C8 C7 H7A 108.7 . .
C6 C7 H7B 108.7 . .
C8 C7 H7B 108.7 . .
H7A C7 H7B 107.6 . .
O1 C8 C9 120.50(9) . .
O1 C8 C7 121.41(10) . .
C9 C8 C7 118.09(9) . .
C10 C9 C14 118.83(10) . .
C10 C9 C8 122.27(9) . .
C14 C9 C8 118.90(9) . .
C11 C10 C9 120.53(10) . .
C11 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C12 C11 C10 119.97(10) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C13 C12 C11 120.10(10) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C14 C13 C12 120.14(10) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C14 C9 120.42(10) . .
C13 C14 H14 119.8 . .
C9 C14 H14 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.3853(13) 2
N1 C5 1.3854(13) .
N1 C4 1.4184(19) .
O1 C8 1.2205(13) .
C1 C2 1.3805(16) .
C1 C2 1.3805(16) 2
C1 H1 0.9500 .
C2 C3 1.3866(17) .
C2 H2 0.9500 .
C3 C4 1.3938(14) .
C3 H3 0.9500 .
C4 C3 1.3939(14) 2
C5 C6 1.3613(15) .
C5 H5 0.9500 .
C6 C6 1.426(2) 2
C6 C7 1.4939(14) .
C7 C8 1.5258(15) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.4937(15) .
C9 C10 1.3944(15) .
C9 C14 1.3999(15) .
C10 C11 1.3856(16) .
C10 H10 0.9500 .
C11 C12 1.3853(16) .
C11 H11 0.9500 .
C12 C13 1.3848(16) .
C12 H12 0.9500 .
C13 C14 1.3818(16) .
C13 H13 0.9500 .
C14 H14 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
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 0.49(8) 2 .
C1 C2 C3 C4 -0.98(16) . .
C2 C3 C4 C3 0.48(8) . 2
C2 C3 C4 N1 -179.52(8) . .
C5 N1 C4 C3 2.68(7) 2 .
C5 N1 C4 C3 -177.32(7) . .
C5 N1 C4 C3 -177.31(7) 2 2
C5 N1 C4 C3 2.68(7) . 2
C5 N1 C5 C6 0.24(5) 2 .
C4 N1 C5 C6 -179.76(5) . .
N1 C5 C6 C6 -0.60(13) . 2
N1 C5 C6 C7 178.41(8) . .
C5 C6 C7 C8 -103.41(12) . .
C6 C6 C7 C8 75.42(15) 2 .
C6 C7 C8 O1 -2.04(14) . .
C6 C7 C8 C9 178.36(9) . .
O1 C8 C9 C10 -173.80(10) . .
C7 C8 C9 C10 5.81(15) . .
O1 C8 C9 C14 6.71(15) . .
C7 C8 C9 C14 -173.68(9) . .
C14 C9 C10 C11 -0.87(16) . .
C8 C9 C10 C11 179.64(10) . .
C9 C10 C11 C12 0.08(17) . .
C10 C11 C12 C13 0.90(17) . .
C11 C12 C13 C14 -1.07(17) . .
C12 C13 C14 C9 0.26(17) . .
C10 C9 C14 C13 0.70(16) . .
C8 C9 C14 C13 -179.79(9) . .
