Bilirubin and its crystal forms
Bracken, Matthew L.; Fernandes, Manuel A.; Mathura, Sadhna; CrystEngComm 26 (2024) 2136–2142; doi:10.1039/D4CE00123K

data_7248347
_publ_section_title
;
 Bilirubin and its crystal forms
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2136
_journal_page_last               2142
_journal_paper_doi               10.1039/D4CE00123K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '1(C33 H36 N4 O6), 0.25[]'
_chemical_formula_sum            'C33 H36 N4 O6'
_chemical_formula_weight         584.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-06 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                98.973(3)
_cell_angle_beta                 104.421(3)
_cell_angle_gamma                111.029(3)
_cell_formula_units_Z            4
_cell_length_a                   11.8077(10)
_cell_length_b                   15.0220(12)
_cell_length_c                   19.3471(17)
_cell_measurement_reflns_used    7142
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      18.42
_cell_measurement_theta_min      2.26
_cell_volume                     2985.8(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2197
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            161376
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.621
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1055 before and 0.0770 after correction.
The Ratio of minimum to maximum transmission is 0.8279.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       Block
_exptl_crystal_F_000             1240
_exptl_crystal_recrystallization_method
'Vapour diffusion of diethyl ether into pyridine'
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     808
_refine_ls_number_reflns         10506
_refine_ls_number_restraints     213
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1867
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1243P)^2^+3.8292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4945
_reflns_number_total             10506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00123k3.cif
_cod_data_source_block           Form2_23mbb_sadnah16_ns16_bilpyether
_cod_depositor_comments
'Adding full bibliography for 7248346--7248347.cif.'
_cod_database_code               7248347
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C65-C66 \\sim C64-C66B \\sim C35-C34 \\sim C40-C34B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C39 \\sim C36 \\sim C37 \\sim C35 \\sim C34: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C38 \\sim C37 \\sim C36 \\sim C40 \\sim C34B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C60 \\sim C61 \\sim C62 \\sim C64 \\sim C66B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C61 \\sim C62 \\sim C63 \\sim C65 \\sim C66: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C5 \\sim C4 \\sim C3 \\sim C6: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C39, C36, C37, C35, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C38, C37, C36, C40, C34B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C60, C61, C62, C64, C66B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C61, C62, C63, C65, C66
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5, C4, C3, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(H40)=Sof(H64)=Sof(H65A)=Sof(H65B)=Sof(H65C)=
 Sof(C34B)=Sof(H34C)=Sof(H34D)=Sof(C66B)=Sof(H66C)=Sof(H66D)=1-FVAR(1)
 Sof(H35)=Sof(H40A)=Sof(H40B)=Sof(H40C)=Sof(H64A)=Sof(H64B)=Sof(H64C)=Sof(H65)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C66)=Sof(H66A)=Sof(H66B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C22(H22A,H22B), C23(H23A,
 H23B), C47(H47A,H47B), C48(H48A,H48B), C50(H50A,H50B), C55(H55A,H55B),
 C56(H56A,H56B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3A), N4(H4), C2(H2A), C8(H8A), C26(H26), C31(H31), N5(H5),
  N6(H6), N7(H7), N8(H8), C35(H35), C40(H40), C41(H41), C59(H59), C64(H64),
 C65(H65)
6.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C32(H32A,H32B), C34(H34A,H34B), C66(H66A,H66B), C34B(H34C,H34D),
 C66B(H66C,H66D)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C33(H33A,H33B,
 H33C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C), C46(H46A,H46B,H46C), C58(H58A,
 H58B,H58C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6A), O9(H9), O12(H12)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              82073
_shelx_fab_checksum              75531
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'