#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234723.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_7234723
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            'C29 H21 N3 O8'
_chemical_formula_weight         539.49
_chemical_name_common            SSB-14-17
_chemical_name_systematic        Nelson05
_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                 90.7780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0196(3)
_cell_length_b                   13.8603(4)
_cell_length_c                   12.8511(4)
_cell_measurement_reflns_used    7538
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.62
_cell_volume                     2496.94(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0381
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25296
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_min         2.066
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       rod
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.7400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4871
_reflns_number_total             6198
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-3995.cif
_cod_data_source_block           nelson05
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7234723
_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   0.878
_shelx_estimated_absorpt_t_max   0.938
_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 -0.47803(8) -0.32327(8) 0.99943(9) 0.0356(3) Uani 1 1 d . . . . .
O2 O -0.55456(7) -0.19384(9) 1.04135(9) 0.0342(3) Uani 1 1 d . . . . .
O3 O -0.12344(6) 0.22171(7) 1.00191(7) 0.0208(2) Uani 1 1 d . . . . .
O4 O -0.01108(7) 0.37816(6) 0.96731(7) 0.0209(2) Uani 1 1 d . . . . .
O5 O 0.26016(7) -0.09496(7) 0.73426(8) 0.0287(2) Uani 1 1 d . . . . .
O6 O 0.31137(7) 0.03270(7) 0.64241(8) 0.0257(2) Uani 1 1 d . . . . .
O7 O 0.45809(8) 0.81086(8) 0.79396(9) 0.0361(3) Uani 1 1 d . . . . .
O8 O 0.55953(8) 0.70614(9) 0.73746(9) 0.0374(3) Uani 1 1 d . . . . .
N1 N -0.48217(8) -0.23590(9) 1.01375(9) 0.0263(3) Uani 1 1 d . . . . .
N2 N 0.10560(8) 0.03027(7) 0.80361(8) 0.0181(2) Uani 1 1 d . . . . .
N3 N 0.48043(9) 0.72825(9) 0.76983(9) 0.0283(3) Uani 1 1 d . . . . .
C1 C 0.01840(12) 0.39034(11) 1.07379(11) 0.0311(3) Uani 1 1 d . . . . .
H16 H -0.0072 0.3375 1.1157 0.047 Uiso 1 1 calc R U . . .
H17 H -0.0057 0.4520 1.0999 0.047 Uiso 1 1 calc R U . . .
H15 H 0.0882 0.3899 1.0785 0.047 Uiso 1 1 calc R U . . .
C2 C 0.40864(10) 0.65164(10) 0.78224(10) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.31779(10) 0.67663(10) 0.81230(11) 0.0239(3) Uani 1 1 d . . . . .
H18 H 0.3005 0.7423 0.8214 0.029 Uiso 1 1 calc R U . . .
C4 C 0.25243(10) 0.60331(9) 0.82884(11) 0.0226(3) Uani 1 1 d . . . . .
H19 H 0.1895 0.6187 0.8497 0.027 Uiso 1 1 calc R U . . .
C5 C 0.27865(9) 0.50648(9) 0.81500(10) 0.0199(3) Uani 1 1 d . . . . .
C6 C 0.21286(9) 0.42983(9) 0.83591(10) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.16047(9) 0.36366(9) 0.85407(10) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.09996(9) 0.28238(9) 0.87132(10) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.12437(9) 0.19017(9) 0.83154(10) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.06342(9) 0.11005(9) 0.84737(10) 0.0170(3) Uani 1 1 d . . . . .
C11 C -0.02310(9) 0.11897(9) 0.90173(10) 0.0176(3) Uani 1 1 d . . . . .
C12 C -0.09092(9) 0.04430(9) 0.91851(10) 0.0186(3) Uani 1 1 d . . . . .
C13 C -0.15579(9) -0.00963(9) 0.93631(10) 0.0199(3) Uani 1 1 d . . . . .
C14 C -0.23683(9) -0.06879(9) 0.95772(10) 0.0191(3) Uani 1 1 d . . . . .
C15 C -0.23789(10) -0.16717(9) 0.93237(10) 0.0210(3) Uani 1 1 d . . . . .
H11 H -0.1835 -0.1958 0.9016 0.025 Uiso 1 1 calc R U . . .
C16 C -0.31769(10) -0.22289(10) 0.95193(10) 0.0225(3) Uani 1 1 d . . . . .
H10 H -0.3187 -0.2898 0.9357 0.027 Uiso 1 1 calc R U . . .
C17 C -0.39580(9) -0.17849(10) 0.99573(10) 0.0218(3) Uani 1 1 d . . . . .
C18 C 0.43616(10) 0.55705(11) 0.76504(11) 0.0256(3) Uani 1 1 d . . . . .
H21 H 0.4988 0.5425 0.7424 0.031 Uiso 1 1 calc R U . . .
C19 C 0.37058(10) 0.48427(10) 0.78147(11) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.3880 0.4190 0.7700 0.029 Uiso 1 1 calc R U . . .
C20 C 0.19093(9) 0.05972(9) 0.76093(10) 0.0188(3) Uani 1 1 d . . . . .
C21 C 0.20412(9) 0.15699(9) 0.77623(10) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.2567 0.1945 0.7539 0.022 Uiso 1 1 calc R U . . .
C22 C 0.25624(9) -0.01015(9) 0.71290(10) 0.0205(3) Uani 1 1 d . . . . .
C23 C 0.37596(10) -0.03162(11) 0.58838(12) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.4119 -0.0702 0.6394 0.042 Uiso 1 1 calc R U . . .
H3 H 0.4204 0.0065 0.5469 0.042 Uiso 1 1 calc R U . . .
H4 H 0.3391 -0.0745 0.5425 0.042 Uiso 1 1 calc R U . . .
C24 C 0.06327(10) -0.06609(9) 0.79585(11) 0.0228(3) Uani 1 1 d . . . . .
H7 H 0.0824 -0.1044 0.8567 0.034 Uiso 1 1 calc R U . . .
H6 H 0.0854 -0.0978 0.7325 0.034 Uiso 1 1 calc R U . . .
H5 H -0.0064 -0.0605 0.7932 0.034 Uiso 1 1 calc R U . . .
C25 C -0.39682(10) -0.08161(10) 1.02253(11) 0.0237(3) Uani 1 1 d . . . . .
H8 H -0.4516 -0.0536 1.0531 0.028 Uiso 1 1 calc R U . . .
C26 C -0.31672(10) -0.02664(10) 1.00388(11) 0.0227(3) Uani 1 1 d . . . . .
H9 H -0.3157 0.0397 1.0223 0.027 Uiso 1 1 calc R U . . .
C27 C -0.04371(9) 0.21031(9) 0.94252(10) 0.0178(3) Uani 1 1 d . . . . .
C28 C -0.20725(11) 0.24516(13) 0.94146(13) 0.0356(4) Uani 1 1 d . . . . .
H12 H -0.1990 0.3084 0.9088 0.053 Uiso 1 1 calc R U . . .
H14 H -0.2628 0.2469 0.9869 0.053 Uiso 1 1 calc R U . . .
H13 H -0.2172 0.1961 0.8874 0.053 Uiso 1 1 calc R U . . .
C29 C 0.01620(9) 0.29049(9) 0.92744(10) 0.0180(3) Uani 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'
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
C27 O3 C28 113.07(11) . .
C29 O4 C1 112.43(10) . .
C22 O6 C23 114.87(11) . .
O1 N1 O2 123.61(12) . .
O1 N1 C17 118.05(12) . .
O2 N1 C17 118.34(12) . .
C10 N2 C20 107.64(10) . .
C10 N2 C24 125.74(11) . .
C20 N2 C24 126.41(11) . .
O7 N3 O8 123.55(12) . .
O7 N3 C2 117.89(13) . .
O8 N3 C2 118.55(13) . .
C3 C2 C18 122.84(13) . .
C3 C2 N3 118.94(13) . .
C18 C2 N3 118.21(13) . .
C2 C3 C4 118.24(13) . .
C3 C4 C5 120.45(13) . .
C19 C5 C4 119.57(12) . .
C19 C5 C6 119.48(12) . .
C4 C5 C6 120.95(12) . .
C7 C6 C5 177.74(14) . .
C6 C7 C8 177.15(14) . .
C29 C8 C9 117.95(11) . .
C29 C8 C7 121.58(12) . .
C9 C8 C7 120.47(12) . .
C21 C9 C10 107.49(11) . .
C21 C9 C8 132.19(12) . .
C10 C9 C8 120.31(12) . .
N2 C10 C11 130.39(11) . .
N2 C10 C9 107.89(11) . .
C11 C10 C9 121.70(11) . .
C27 C11 C10 116.51(11) . .
C27 C11 C12 117.28(12) . .
C10 C11 C12 126.20(11) . .
C13 C12 C11 171.78(14) . .
C12 C13 C14 176.48(14) . .
C15 C14 C26 119.84(12) . .
C15 C14 C13 121.24(12) . .
C26 C14 C13 118.91(12) . .
C16 C15 C14 120.41(13) . .
C17 C16 C15 118.15(12) . .
C16 C17 C25 122.90(12) . .
C16 C17 N1 118.81(12) . .
C25 C17 N1 118.29(12) . .
C19 C18 C2 118.60(13) . .
C18 C19 C5 120.25(13) . .
C21 C20 N2 110.36(11) . .
C21 C20 C22 128.40(12) . .
N2 C20 C22 121.14(11) . .
C20 C21 C9 106.61(11) . .
O5 C22 O6 124.11(13) . .
O5 C22 C20 124.80(13) . .
O6 C22 C20 111.08(11) . .
C26 C25 C17 118.70(13) . .
C25 C26 C14 119.98(13) . .
O3 C27 C11 119.07(11) . .
O3 C27 C29 118.56(11) . .
C11 C27 C29 122.34(12) . .
O4 C29 C8 120.38(11) . .
O4 C29 C27 118.47(12) . .
C8 C29 C27 121.13(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.2264(16) .
O2 N1 1.2270(16) .
O3 C27 1.3711(16) .
O3 C28 1.4371(17) .
O4 C29 1.3751(15) .
O4 C1 1.4340(17) .
O5 C22 1.2081(16) .
O6 C22 1.3379(16) .
O6 C23 1.4539(16) .
O7 N3 1.2279(17) .
O8 N3 1.2286(17) .
N1 C17 1.4698(17) .
N2 C10 1.3776(16) .
N2 C20 1.3844(17) .
N2 C24 1.4644(16) .
N3 C2 1.4732(17) .
C2 C3 1.380(2) .
C2 C18 1.385(2) .
C3 C4 1.3866(19) .
C4 C5 1.4035(18) .
C5 C19 1.3987(19) .
C5 C6 1.4348(18) .
C6 C7 1.1998(19) .
C7 C8 1.4294(18) .
C8 C29 1.3909(19) .
C8 C9 1.4201(17) .
C9 C21 1.4101(18) .
C9 C10 1.4175(17) .
C10 C11 1.4133(18) .
C11 C27 1.4019(17) .
C11 C12 1.4237(18) .
C12 C13 1.2015(18) .
C13 C14 1.4310(18) .
C14 C15 1.4020(18) .
C14 C26 1.4021(19) .
C15 C16 1.3853(19) .
C16 C17 1.383(2) .
C17 C25 1.3864(19) .
C18 C19 1.383(2) .
C20 C21 1.3745(18) .
C20 C22 1.4739(18) .
C25 C26 1.3807(19) .
C27 C29 1.4080(18) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132513811
