#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234722.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_7234722
loop_
_publ_author_name
'Subhashini Selvaraju'
'Santosh Adhikari'
'RaiAnna A. Hopson'
'Shuo Dai'
'Arnold L. Rheingold'
'Mario F. Borunda'
'Toby L. Nelson'
_publ_section_title
;
 Effects of structural variations on the optical and electronic properties
 of eumelanin-inspired small molecules
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3995
_journal_page_last               3999
_journal_paper_doi               10.1039/C5TC03982G
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C37 H39 N O4'
_chemical_formula_weight         561.69
_chemical_name_common            SSB-10-102
_chemical_name_systematic        Nelson04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 98.592(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4721(7)
_cell_length_b                   20.8688(13)
_cell_length_c                   14.2792(10)
_cell_measurement_reflns_used    4360
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.20
_cell_volume                     3085.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.435
_diffrn_reflns_theta_min         1.952
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0680P)²+0.8700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4826
_reflns_number_total             7665
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-3995.cif
_cod_data_source_block           nelson04
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7234722
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21646(13) 0.16938(7) 0.30543(9) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.34702(12) 0.13238(7) 0.47814(9) 0.0211(3) Uani 1 1 d . . . . .
O3 O -0.18676(14) -0.14131(7) 0.30286(10) 0.0288(3) Uani 1 1 d . . . . .
O4 O -0.07964(15) -0.17815(7) 0.44010(11) 0.0328(4) Uani 1 1 d . . . . .
N1 N 0.08719(16) -0.06498(8) 0.44493(11) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.5453(3) -0.08758(12) 1.07128(14) 0.0378(6) Uani 1 1 d . . . . .
H36 H 0.4512 -0.0916 1.0647 0.057 Uiso 1 1 calc R U . . .
H1 H 0.5688 -0.0422 1.0703 0.057 Uiso 1 1 calc R U . . .
H37 H 0.5846 -0.1067 1.1314 0.057 Uiso 1 1 calc R U . . .
C2 C 0.59470(19) -0.12249(10) 0.98865(13) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.53583(18) -0.09039(9) 0.89532(13) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.40172(18) -0.09102(10) 0.86762(13) 0.0225(4) Uani 1 1 d . . . . .
H4 H 0.3486 -0.1121 0.9064 0.027 Uiso 1 1 calc R U . . .
C5 C 0.34464(19) -0.06143(10) 0.78463(14) 0.0243(4) Uani 1 1 d . . . . .
H5 H 0.2535 -0.0627 0.7674 0.029 Uiso 1 1 calc R U . . .
C6 C 0.42042(19) -0.02967(9) 0.72617(13) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.36059(19) -0.00199(10) 0.63806(13) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.30532(18) 0.01565(9) 0.56246(13) 0.0207(4) Uani 1 1 d . . . . .
C9 C 0.23589(18) 0.03235(9) 0.47145(12) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.13933(18) -0.00771(9) 0.42056(13) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.07571(17) 0.00992(9) 0.32946(13) 0.0188(4) Uani 1 1 d . . . . .
C12 C 0.10284(17) 0.06902(9) 0.28753(12) 0.0173(4) Uani 1 1 d . . . . .
C13 C 0.03787(17) 0.08770(9) 0.19638(13) 0.0198(4) Uani 1 1 d . . . . .
C14 C -0.01479(18) 0.10204(9) 0.11906(13) 0.0198(4) Uani 1 1 d . . . . .
C15 C -0.07752(17) 0.12343(9) 0.02739(13) 0.0191(4) Uani 1 1 d . . . . .
C16 C -0.07914(19) 0.18833(10) 0.00470(13) 0.0219(4) Uani 1 1 d . . . . .
H20 H -0.0358 0.2181 0.0487 0.026 Uiso 1 1 calc R U . . .
C17 C -0.14314(19) 0.20984(10) -0.08125(13) 0.0230(4) Uani 1 1 d . . . . .
H19 H -0.1434 0.2544 -0.0948 0.028 Uiso 1 1 calc R U . . .
C18 C -0.20753(17) 0.16789(9) -0.14891(12) 0.0189(4) Uani 1 1 d . . . . .
C19 C -0.28310(19) 0.19482(10) -0.24104(13) 0.0232(4) Uani 1 1 d . . . . .
C20 C -0.3534(2) 0.14170(12) -0.30303(15) 0.0378(6) Uani 1 1 d . . . . .
H18 H -0.4117 0.1187 -0.2670 0.057 Uiso 1 1 calc R U . . .
H17 H -0.2899 0.1117 -0.3219 0.057 Uiso 1 1 calc R U . . .
H2 H -0.4034 0.1608 -0.3597 0.057 Uiso 1 1 calc R U . . .
C21 C 0.7421(2) -0.12041(14) 1.00378(18) 0.0477(7) Uani 1 1 d . . . . .
H38 H 0.7757 -0.1430 1.0624 0.072 Uiso 1 1 calc R U . . .
H3 H 0.7712 -0.0757 1.0084 0.072 Uiso 1 1 calc R U . . .
H39 H 0.7741 -0.1411 0.9502 0.072 Uiso 1 1 calc R U . . .
C22 C 0.60980(19) -0.05917(9) 0.83596(13) 0.0204(4) Uani 1 1 d . . . . .
H32 H 0.7011 -0.0586 0.8525 0.025 Uiso 1 1 calc R U . . .
C23 C 0.55374(19) -0.02883(9) 0.75312(13) 0.0215(4) Uani 1 1 d . . . . .
H31 H 0.6069 -0.0074 0.7147 0.026 Uiso 1 1 calc R U . . .
C24 C 0.1277(2) -0.10115(12) 0.53191(16) 0.0413(6) Uani 1 1 d . . . . .
H7 H 0.2039 -0.1269 0.5249 0.062 Uiso 1 1 calc R U . . .
H6 H 0.0574 -0.1295 0.5442 0.062 Uiso 1 1 calc R U . . .
H8 H 0.1489 -0.0714 0.5850 0.062 Uiso 1 1 calc R U . . .
C25 C -0.00890(18) -0.08265(10) 0.37134(13) 0.0210(4) Uani 1 1 d . . . . .
C26 C -0.01651(18) -0.03833(9) 0.29975(14) 0.0197(4) Uani 1 1 d . . . . .
H27 H -0.0731 -0.0398 0.2412 0.024 Uiso 1 1 calc R U . . .
C27 C -0.2005(2) 0.10294(10) -0.12711(14) 0.0271(5) Uani 1 1 d . . . . .
H10 H -0.2398 0.0730 -0.1726 0.032 Uiso 1 1 calc R U . . .
C28 C -0.1375(2) 0.08056(10) -0.04061(14) 0.0281(5) Uani 1 1 d . . . . .
H9 H -0.1352 0.0359 -0.0277 0.034 Uiso 1 1 calc R U . . .
C29 C -0.3828(2) 0.24313(11) -0.21592(15) 0.0297(5) Uani 1 1 d . . . . .
H11 H -0.3383 0.2786 -0.1797 0.045 Uiso 1 1 calc R U . . .
H13 H -0.4408 0.2219 -0.1777 0.045 Uiso 1 1 calc R U . . .
H12 H -0.4332 0.2598 -0.2742 0.045 Uiso 1 1 calc R U . . .
C30 C -0.1909(2) 0.22907(12) -0.29884(15) 0.0366(6) Uani 1 1 d . . . . .
H14 H -0.2395 0.2444 -0.3586 0.055 Uiso 1 1 calc R U . . .
H16 H -0.1239 0.1991 -0.3122 0.055 Uiso 1 1 calc R U . . .
H15 H -0.1505 0.2655 -0.2625 0.055 Uiso 1 1 calc R U . . .
C31 C 0.19269(18) 0.10944(9) 0.33998(13) 0.0185(4) Uani 1 1 d . . . . .
C32 C 0.1431(2) 0.21785(10) 0.34601(16) 0.0340(5) Uani 1 1 d . . . . .
H23 H 0.0507 0.2082 0.3307 0.051 Uiso 1 1 calc R U . . .
H22 H 0.1606 0.2598 0.3200 0.051 Uiso 1 1 calc R U . . .
H21 H 0.1681 0.2184 0.4149 0.051 Uiso 1 1 calc R U . . .
C33 C 0.25973(17) 0.09047(9) 0.42897(12) 0.0179(4) Uani 1 1 d . . . . .
C34 C 0.46617(19) 0.13724(10) 0.44023(14) 0.0265(5) Uani 1 1 d . . . . .
H24 H 0.5141 0.0969 0.4510 0.040 Uiso 1 1 calc R U . . .
H26 H 0.5181 0.1723 0.4717 0.040 Uiso 1 1 calc R U . . .
H25 H 0.4477 0.1458 0.3721 0.040 Uiso 1 1 calc R U . . .
C35 C -0.09215(19) -0.13879(10) 0.37702(14) 0.0247(4) Uani 1 1 d . . . . .
C36 C -0.2844(2) -0.18949(12) 0.31174(17) 0.0361(6) Uani 1 1 d . . . . .
H29 H -0.2429 -0.2314 0.3234 0.054 Uiso 1 1 calc R U . . .
H30 H -0.3462 -0.1911 0.2531 0.054 Uiso 1 1 calc R U . . .
H28 H -0.3298 -0.1784 0.3648 0.054 Uiso 1 1 calc R U . . .
C37 C 0.5529(2) -0.19268(10) 0.98881(15) 0.0323(5) Uani 1 1 d . . . . .
H35 H 0.5815 -0.2150 0.9352 0.048 Uiso 1 1 calc R U . . .
H33 H 0.4586 -0.1950 0.9832 0.048 Uiso 1 1 calc R U . . .
H34 H 0.5918 -0.2130 1.0481 0.048 Uiso 1 1 calc R U . . .
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
C31 O1 C32 110.87(15) . .
C33 O2 C34 113.58(14) . .
C35 O3 C36 113.91(16) . .
C10 N1 C25 107.93(15) . .
C10 N1 C24 125.89(17) . .
C25 N1 C24 126.17(18) . .
C21 C2 C37 108.11(19) . .
C21 C2 C3 112.11(17) . .
C37 C2 C3 109.95(16) . .
C21 C2 C1 109.03(19) . .
C37 C2 C1 108.85(18) . .
C3 C2 C1 108.73(16) . .
C22 C3 C4 117.25(17) . .
C22 C3 C2 123.00(17) . .
C4 C3 C2 119.75(17) . .
C5 C4 C3 121.45(18) . .
C4 C5 C6 120.56(18) . .
C23 C6 C5 118.37(17) . .
C23 C6 C7 121.61(18) . .
C5 C6 C7 119.93(18) . .
C8 C7 C6 173.9(2) . .
C7 C8 C9 176.1(2) . .
C33 C9 C10 116.60(16) . .
C33 C9 C8 120.38(17) . .
C10 C9 C8 123.01(18) . .
N1 C10 C11 107.84(16) . .
N1 C10 C9 131.07(17) . .
C11 C10 C9 121.05(18) . .
C26 C11 C12 131.52(17) . .
C26 C11 C10 107.23(17) . .
C12 C11 C10 121.09(17) . .
C31 C12 C11 117.43(16) . .
C31 C12 C13 120.99(17) . .
C11 C12 C13 121.55(17) . .
C14 C13 C12 178.2(2) . .
C13 C14 C15 176.5(2) . .
C16 C15 C28 118.18(17) . .
C16 C15 C14 119.97(17) . .
C28 C15 C14 121.85(18) . .
C17 C16 C15 120.66(18) . .
C16 C17 C18 121.95(19) . .
C27 C18 C17 116.82(17) . .
C27 C18 C19 123.47(17) . .
C17 C18 C19 119.70(17) . .
C29 C19 C20 108.97(17) . .
C29 C19 C18 108.79(15) . .
C20 C19 C18 111.75(17) . .
C29 C19 C30 108.94(18) . .
C20 C19 C30 108.16(18) . .
C18 C19 C30 110.19(16) . .
C23 C22 C3 121.85(18) . .
C6 C23 C22 120.51(18) . .
C26 C25 N1 109.81(17) . .
C26 C25 C35 127.56(18) . .
N1 C25 C35 122.51(17) . .
C25 C26 C11 107.17(17) . .
C18 C27 C28 121.89(18) . .
C27 C28 C15 120.40(19) . .
O1 C31 C12 119.93(16) . .
O1 C31 C33 118.88(17) . .
C12 C31 C33 121.19(17) . .
O2 C33 C9 118.55(16) . .
O2 C33 C31 118.86(17) . .
C9 C33 C31 122.49(17) . .
O4 C35 O3 123.13(19) . .
O4 C35 C25 125.61(19) . .
O3 C35 C25 111.26(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C31 1.381(2) .
O1 C32 1.443(3) .
O2 C33 1.379(2) .
O2 C34 1.436(2) .
O3 C35 1.339(2) .
O3 C36 1.453(3) .
O4 C35 1.212(2) .
N1 C10 1.380(3) .
N1 C25 1.392(2) .
N1 C24 1.461(3) .
C1 C2 1.540(3) .
C2 C21 1.527(3) .
C2 C37 1.529(3) .
C2 C3 1.536(2) .
C3 C22 1.393(3) .
C3 C4 1.401(3) .
C4 C5 1.390(3) .
C5 C6 1.401(3) .
C6 C23 1.392(3) .
C6 C7 1.440(3) .
C7 C8 1.204(3) .
C8 C9 1.434(2) .
C9 C33 1.395(3) .
C9 C10 1.425(3) .
C10 C11 1.419(2) .
C11 C26 1.416(3) .
C11 C12 1.418(3) .
C12 C31 1.395(3) .
C12 C13 1.430(3) .
C13 C14 1.196(3) .
C14 C15 1.445(3) .
C15 C16 1.392(3) .
C15 C28 1.398(3) .
C16 C17 1.382(3) .
C17 C18 1.400(3) .
C18 C27 1.390(3) .
C18 C19 1.537(3) .
C19 C29 1.532(3) .
C19 C20 1.536(3) .
C19 C30 1.537(3) .
C22 C23 1.392(3) .
C25 C26 1.372(3) .
C25 C35 1.470(3) .
C27 C28 1.391(3) .
C31 C33 1.413(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132513809
