#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:51:18 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243582 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/62/1556231.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_1556231
loop_
_publ_author_name
'Klopfleisch, Maurice'
'Seidel, Raphael A.'
'Görls, Helmar'
'Richter, Hannes'
'Beckert, Rainer'
'Imhof, Wolfgang'
'Reiher, Markus'
'Pohnert, Georg'
'Westerhausen, Matthias'
_publ_section_title
;
 Total synthesis and detection of the bilirubin oxidation product
 (Z)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide
 (Z-BOX A).
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4608
_journal_page_last               4611
_journal_paper_doi               10.1021/ol402221b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                76.256(7)
_cell_angle_beta                 81.880(7)
_cell_angle_gamma                79.808(7)
_cell_formula_units_Z            2
_cell_length_a                   3.9281(5)
_cell_length_b                   9.3038(9)
_cell_length_c                   13.2519(11)
_cell_measurement_reflns_used    3100
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.49
_cell_volume                     460.52(8)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + 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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3100
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.49
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0464
_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)+(0.0532P)²+0.0466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                1482
_reflns_number_total             2041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402221b_si_001.cif
_cod_data_source_block           FO4070
_cod_database_code               1556231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.1648(3) 0.62940(12) 0.69710(9) 0.0208(3) Uani 1 1 d
O2 O 0.4311(3) 0.47826(13) 0.83195(10) 0.0296(3) Uani 1 1 d
O3 O -0.2345(3) 0.86074(13) 0.41368(9) 0.0268(3) Uani 1 1 d
O4 O 0.1372(3) 0.66638(12) 0.48991(9) 0.0225(3) Uani 1 1 d
C1 C 0.2457(4) 0.59275(18) 0.79988(13) 0.0220(4) Uani 1 1 d
C2 C 0.0751(4) 0.71429(18) 0.85174(13) 0.0203(4) Uani 1 1 d
C3 C -0.1020(4) 0.81952(18) 0.78024(13) 0.0190(4) Uani 1 1 d
C4 C -0.0460(4) 0.76687(17) 0.68226(12) 0.0178(4) Uani 1 1 d
C5 C 0.1176(5) 0.7066(2) 0.96265(14) 0.0254(4) Uani 1 1 d
H5A H -0.107(6) 0.730(2) 1.0013(18) 0.047(6) Uiso 1 1 d
H5B H 0.275(6) 0.779(3) 0.9689(18) 0.054(7) Uiso 1 1 d
H5C H 0.224(6) 0.608(3) 0.9942(17) 0.043(6) Uiso 1 1 d
C6 C -0.3109(4) 0.96319(18) 0.78959(13) 0.0220(4) Uani 1 1 d
H6 H -0.468(5) 1.004(2) 0.7379(16) 0.029(5) Uiso 1 1 d
C7 C -0.3011(5) 1.0375(2) 0.86195(15) 0.0315(5) Uani 1 1 d
H7A H -0.441(5) 1.136(2) 0.8603(15) 0.028(5) Uiso 1 1 d
H7B H -0.136(6) 1.001(3) 0.9144(19) 0.051(6) Uiso 1 1 d
C8 C -0.1667(4) 0.83615(18) 0.59090(13) 0.0192(4) Uani 1 1 d
H8A H -0.319(5) 0.930(2) 0.5898(13) 0.017(4) Uiso 1 1 d
C9 C -0.0952(4) 0.78928(17) 0.49023(13) 0.0185(4) Uani 1 1 d
C10 C 0.2287(5) 0.6249(2) 0.38928(14) 0.0233(4) Uani 1 1 d
H10A H 0.347(5) 0.704(2) 0.3392(17) 0.036(5) Uiso 1 1 d
H10B H 0.022(5) 0.607(2) 0.3642(15) 0.031(5) Uiso 1 1 d
H10C H 0.393(5) 0.537(2) 0.4047(15) 0.031(5) Uiso 1 1 d
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'
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
C4 O1 C1 107.66(12)
C9 O4 C10 115.39(12)
O2 C1 O1 120.56(16)
O2 C1 C2 130.84(16)
O1 C1 C2 108.60(13)
C3 C2 C1 107.27(15)
C3 C2 C5 131.99(16)
C1 C2 C5 120.74(14)
C2 C3 C6 130.18(16)
C2 C3 C4 107.58(14)
C6 C3 C4 122.23(14)
C8 C4 O1 123.10(15)
C8 C4 C3 128.00(15)
O1 C4 C3 108.89(12)
C2 C5 H5A 110.4(13)
C2 C5 H5B 111.5(14)
H5A C5 H5B 108.7(19)
C2 C5 H5C 109.9(13)
H5A C5 H5C 109.1(19)
H5B C5 H5C 107.2(18)
C7 C6 C3 126.11(16)
C7 C6 H6 118.9(12)
C3 C6 H6 115.0(12)
C6 C7 H7A 120.8(11)
C6 C7 H7B 121.1(14)
H7A C7 H7B 117.8(18)
C4 C8 C9 128.64(16)
C4 C8 H8A 116.3(10)
C9 C8 H8A 115.1(10)
O3 C9 O4 123.48(15)
O3 C9 C8 121.70(15)
O4 C9 C8 114.80(13)
O4 C10 H10A 109.8(12)
O4 C10 H10B 109.9(12)
H10A C10 H10B 112.8(16)
O4 C10 H10C 103.0(12)
H10A C10 H10C 108.8(17)
H10B C10 H10C 112.2(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3827(19)
O1 C1 1.3912(19)
O2 C1 1.201(2)
O3 C9 1.2157(19)
O4 C9 1.3314(19)
O4 C10 1.455(2)
C1 C2 1.474(3)
C2 C3 1.358(2)
C2 C5 1.486(2)
C3 C6 1.462(2)
C3 C4 1.469(2)
C4 C8 1.338(2)
C5 H5A 0.97(3)
C5 H5B 1.02(2)
C5 H5C 0.96(2)
C6 C7 1.317(3)
C6 H6 0.952(19)
C7 H7A 0.97(2)
C7 H7B 0.98(2)
C8 C9 1.475(2)
C8 H8A 0.966(18)
C10 H10A 1.00(2)
C10 H10B 0.97(2)
C10 H10C 0.95(2)
