#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:27:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180263 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/49/7114962.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_7114962
loop_
_publ_author_name
'Che, Chi-Ming'
'Wan, Chun-Wai'
'Lin, Wei-Zhu'
'Yu, Wing-Yiu'
'Zhou, Zhong-Yuan'
'Lai, W.-Y.'
'Lee, S.-T.'
_publ_section_title
;
 Highly luminous substituted bipyrroles
;
_journal_issue                   8
_journal_name_full               'Chemical Communications'
_journal_page_first              721
_journal_paper_doi               10.1039/b009687n
_journal_year                    2001
_chemical_formula_sum            'C32 H32 N2 O8'
_chemical_formula_weight         572.60
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           72
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-I 2 2c'
_symmetry_space_group_name_H-M   'I b a m'
_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            4
_cell_length_a                   14.3634(19)
_cell_length_b                   27.535(4)
_cell_length_c                   7.2722(10)
_cell_measurement_reflns_used    CCD
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     2876.1(7)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR DDIFRACTOMETER'
_diffrn_measurement_method       'PHI and OMEGA SCAN'
_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  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9113
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1674
_reflns_number_gt                1001
_reflns_number_total             1742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b009687n.txt
_cod_data_source_block           w15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        2876.2(7)
_cod_original_sg_symbol_H-M      Ibam
_cod_database_code               7114962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, -z+1/2'
'x+1, -y+1, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'x, -y, z+1/2'
'-x, y, 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
O1 O -0.09185(5) 0.39891(3) 0.5000 0.0600(3) Uani 1 2 d S
O2 O 0.03205(5) 0.35191(3) 0.5000 0.0627(3) Uani 1 2 d S
O3 O 0.35806(5) 0.45883(3) 0.5000 0.0861(4) Uani 1 2 d S
O4 O 0.30841(5) 0.53528(3) 0.5000 0.0735(3) Uani 1 2 d S
N1 N 0.12671(5) 0.50743(3) 0.5000 0.0416(2) Uani 1 2 d S
H1A H 0.1356 0.5403 0.5000 0.050 Uiso 1 2 d S
C1 C 0.06012(7) 0.43471(3) 0.5000 0.0382(3) Uani 1 2 d S
C2 C 0.15816(7) 0.42830(3) 0.5000 0.0411(3) Uani 1 2 d S
C3 C 0.19712(7) 0.47384(4) 0.5000 0.0438(3) Uani 1 2 d S
C4 C 0.04255(6) 0.48544(3) 0.5000 0.0353(3) Uani 1 2 d S
C5 C -0.00772(7) 0.39537(3) 0.5000 0.0405(3) Uani 1 2 d S
C6 C -0.02833(8) 0.30974(4) 0.5000 0.0619(4) Uani 1 2 d S
H6A H -0.0680 0.3098 0.3926 0.074 Uiso 0.50 1 d P
C7 C 0.03639(10) 0.26635(5) 0.5000 0.0749(5) Uani 1 2 d S
H7A H 0.0037(13) 0.2386(6) 0.5000 0.112 Uiso 1 2 d S
H7B H 0.0811(19) 0.2655(8) 0.382(3) 0.112 Uiso 0.50 1 d P
C8 C 0.21126(7) 0.38190(4) 0.5000 0.0455(3) Uani 1 2 d S
C9 C 0.23473(6) 0.35961(3) 0.33665(15) 0.0624(3) Uani 1 1 d .
H9A H 0.2207 0.3747 0.2256 0.075 Uiso 1 1 calc R
C10 C 0.27903(7) 0.31499(3) 0.33662(19) 0.0812(3) Uani 1 1 d .
H10A H 0.2943 0.3001 0.2259 0.097 Uiso 1 1 calc R
C11 C 0.30038(10) 0.29271(5) 0.5000 0.0891(6) Uani 1 2 d S
H11A H 0.3293 0.2625 0.5000 0.107 Uiso 1 2 calc SR
C12 C 0.29631(7) 0.48747(4) 0.5000 0.0548(4) Uani 1 2 d S
C13 C 0.40708(10) 0.55061(6) 0.5000 0.1095(8) Uani 1 2 d S
H13A H 0.4382 0.5377 0.3933 0.131 Uiso 0.50 1 d P
C14 C 0.41635(13) 0.59982(7) 0.5000 0.1603(14) Uani 1 2 d S
H14A H 0.471(3) 0.6107(12) 0.5000 0.240 Uiso 1 2 d S
H14B H 0.396(3) 0.6213(15) 0.5000 0.240 Uiso 1 2 d S
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'
O O 0.0106 0.0060 '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 O2 C6 117.72(8) . .
C12 O4 C13 114.10(9) . .
C4 N1 C3 110.95(8) . .
C2 C1 C4 107.37(8) . .
C2 C1 C5 124.84(9) . .
C4 C1 C5 127.79(9) . .
C3 C2 C1 106.92(9) . .
C3 C2 C8 125.12(9) . .
C1 C2 C8 127.97(9) . .
N1 C3 C2 108.40(9) . .
N1 C3 C12 122.79(9) . .
C2 C3 C12 128.82(9) . .
N1 C4 C1 106.37(8) . .
N1 C4 C4 120.13(11) . 9_566
C1 C4 C4 133.50(11) . 9_566
O1 C5 O2 120.14(9) . .
O1 C5 C1 127.36(9) . .
O2 C5 C1 112.51(9) . .
O2 C6 C7 105.36(9) . .
C9 C8 C9 118.96(10) . 10_556
C9 C8 C2 120.50(5) . .
C9 C8 C2 120.50(5) 10_556 .
C8 C9 C10 120.52(10) . .
C11 C10 C9 119.98(11) . .
C10 C11 C10 120.01(13) 10_556 .
O3 C12 O4 124.12(10) . .
O3 C12 C3 123.59(10) . .
O4 C12 C3 112.29(9) . .
C14 C13 O4 112.19(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.2124(13) .
O2 C5 1.3260(12) .
O2 C6 1.4494(13) .
O3 C12 1.1869(14) .
O4 C12 1.3279(14) .
O4 C13 1.4786(16) .
N1 C4 1.3520(12) .
N1 C3 1.3704(13) .
C1 C2 1.4191(14) .
C1 C4 1.4195(14) .
C1 C5 1.4569(14) .
C2 C3 1.3730(14) .
C2 C8 1.4881(14) .
C3 C12 1.4734(15) .
C4 C4 1.4620(18) 9_566
C6 C7 1.5138(17) .
C8 C9 1.3790(11) .
C8 C9 1.3790(11) 10_556
C9 C10 1.3835(12) .
C10 C11 1.3719(14) .
C11 C10 1.3719(14) 10_556
C13 C14 1.362(3) .
