Toward an amphiphilic bilirubin: the crystal structure of a bilirubin e-isomer.
Dey, Sanjeev K.; Lightner, David A.; The Journal of organic chemistry 73 (2008) 2704–2714; doi:10.1021/jo702593x

data_4029554
_publ_section_title
;
 Toward an amphiphilic bilirubin: the crystal structure of a bilirubin
 e-isomer.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2704
_journal_page_last               2714
_journal_paper_doi               10.1021/jo702593x
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C32.16667 H38.33333 Cl0.33333 N4 O10'
_chemical_formula_weight         652.82
_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                 94.3940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            24
_cell_length_a                   33.8740(15)
_cell_length_b                   15.4808(7)
_cell_length_c                   38.1685(17)
_cell_measurement_reflns_used    5915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.03
_cell_measurement_theta_min      2.20
_cell_volume                     19956.6(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1051
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            82608
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             8280
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.095
_refine_diff_density_max         2.528
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.00029(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1262
_refine_ls_number_reflns         13031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.225
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0984
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3061
_refine_ls_wR_factor_ref         0.3358
_reflns_number_gt                8037
_reflns_number_total             13031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702593x-file003.cif
_cod_data_source_block           skd185m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/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 

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         1958.45
_cod_original_formula_units_Z            8
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C96.50 H115 Cl N12 O30'
_cod_database_code               4029554