#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234634.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_7234634
loop_
_publ_author_name
'Abdelhamid Ghodbane'
'W. Brett Fellows'
'John R. Bright'
'Debashree Ghosh'
'Nathalie Saffon'
'Laren M. Tolbert'
'Suzanne Fery-Forgues'
'Kyril M. Solntsev'
_publ_section_title
;
 Effects of the benzoxazole group on green fluorescent protein chromophore
 crystal structure and solid state photophysics
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2793
_journal_page_last               2801
_journal_paper_doi               10.1039/C5TC03776J
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C30 H37 N3 O2'
_chemical_formula_weight         471.63
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.0030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.4404(9)
_cell_length_b                   7.3304(3)
_cell_length_c                   13.9803(4)
_cell_measurement_reflns_used    6567
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.94
_cell_volume                     2581.77(16)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         micro-focus
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31912
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         5.19
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4855
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.4216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                3435
_reflns_number_total             4855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-2793.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7234634
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.14119(4) 0.65425(15) 0.71607(7) 0.0382(4) Uani 0.846(13) 1 d PU A 1
N1 N 0.18590(4) 0.65262(16) 0.86650(9) 0.0354(4) Uani 0.846(13) 1 d PU A 1
O1' O 0.18590(4) 0.65262(16) 0.86650(9) 0.0354(4) Uani 0.154(13) 1 d PU A 2
N1' N 0.14119(4) 0.65425(15) 0.71607(7) 0.0382(4) Uani 0.154(13) 1 d PU A 2
O2 O 0.46733(4) 0.79146(16) 0.48391(7) 0.0436(3) Uani 1 1 d . . .
N2 N 0.45057(4) 0.74119(17) 0.72940(8) 0.0340(3) Uani 1 1 d . A .
N3 N 0.51605(4) 0.78253(17) 0.63740(8) 0.0308(3) Uani 1 1 d . A .
C1 C 0.18889(5) 0.6591(2) 0.77464(12) 0.0349(4) Uani 1 1 d . . .
C2 C 0.10415(5) 0.6446(2) 0.77946(11) 0.0349(4) Uani 1 1 d . . .
C3 C 0.13147(5) 0.64372(19) 0.87226(11) 0.0328(3) Uani 1 1 d . A .
C4 C 0.10417(6) 0.6364(2) 0.95135(12) 0.0399(4) Uani 1 1 d . . .
H4 H 0.1222 0.6344 1.0156 0.048 Uiso 1 1 calc R A .
C5 C 0.04948(6) 0.6321(2) 0.93221(12) 0.0446(4) Uani 1 1 d . A .
H5 H 0.0295 0.6289 0.9847 0.053 Uiso 1 1 calc R . .
C6 C 0.02281(6) 0.6323(2) 0.83853(13) 0.0489(4) Uani 1 1 d . . .
H6 H -0.0149 0.6282 0.8287 0.059 Uiso 1 1 calc R A .
C7 C 0.04974(6) 0.6383(2) 0.75930(13) 0.0465(4) Uani 1 1 d . A .
H7 H 0.0318 0.6381 0.6950 0.056 Uiso 1 1 calc R . .
C8 C 0.23679(5) 0.67376(19) 0.72900(10) 0.0307(3) Uani 1 1 d . A .
C9 C 0.23402(5) 0.6858(2) 0.62917(10) 0.0336(4) Uani 1 1 d . . .
H9 H 0.2006 0.6801 0.5895 0.040 Uiso 1 1 calc R A .
C10 C 0.27969(5) 0.7061(2) 0.58779(10) 0.0327(3) Uani 1 1 d . A .
H10 H 0.2772 0.7144 0.5195 0.039 Uiso 1 1 calc R . .
C11 C 0.32969(5) 0.71464(19) 0.64385(10) 0.0285(3) Uani 1 1 d . . .
C12 C 0.33220(5) 0.70082(19) 0.74442(10) 0.0305(3) Uani 1 1 d . A .
H12 H 0.3656 0.7057 0.7842 0.037 Uiso 1 1 calc R . .
C13 C 0.28640(5) 0.6802(2) 0.78601(10) 0.0318(3) Uani 1 1 d . . .
H13 H 0.2887 0.6702 0.8542 0.038 Uiso 1 1 calc R A .
C14 C 0.37600(5) 0.73883(19) 0.59504(10) 0.0308(3) Uani 1 1 d . A .
H14 H 0.3688 0.7480 0.5267 0.037 Uiso 1 1 calc R . .
C15 C 0.42762(5) 0.7502(2) 0.63253(9) 0.0298(3) Uani 1 1 d . . .
C16 C 0.47030(5) 0.7767(2) 0.57115(10) 0.0312(3) Uani 1 1 d . A .
C17 C 0.50137(5) 0.7603(2) 0.72868(10) 0.0317(3) Uani 1 1 d . . .
C18 C 0.54172(6) 0.7591(2) 0.81599(10) 0.0418(4) Uani 1 1 d . A .
H18A H 0.5240 0.7528 0.8738 0.063 Uiso 1 1 calc R . .
H18B H 0.5630 0.8709 0.8178 0.063 Uiso 1 1 calc R . .
H18C H 0.5649 0.6529 0.8141 0.063 Uiso 1 1 calc R . .
C19 C 0.56929(5) 0.8127(2) 0.61283(11) 0.0338(4) Uani 1 1 d . . .
H19A H 0.5888 0.8948 0.6616 0.041 Uiso 1 1 calc R A .
H19B H 0.5663 0.8751 0.5495 0.041 Uiso 1 1 calc R . .
C20 C 0.60084(6) 0.6392(2) 0.60800(11) 0.0378(4) Uani 1 1 d . A .
H20A H 0.5829 0.5609 0.5557 0.045 Uiso 1 1 calc R . .
H20B H 0.6017 0.5720 0.6697 0.045 Uiso 1 1 calc R . .
C21 C 0.65763(6) 0.6761(2) 0.58947(10) 0.0386(4) Uani 1 1 d . . .
H21A H 0.6736 0.7677 0.6369 0.046 Uiso 1 1 calc R A .
H21B H 0.6784 0.5621 0.6014 0.046 Uiso 1 1 calc R . .
C22 C 0.66323(5) 0.7438(2) 0.48885(10) 0.0333(3) Uani 1 1 d . A .
H22A H 0.6438 0.8605 0.4774 0.040 Uiso 1 1 calc R . .
H22B H 0.6464 0.6545 0.4410 0.040 Uiso 1 1 calc R . .
C23 C 0.72064(5) 0.7728(2) 0.47243(10) 0.0341(4) Uani 1 1 d . . .
H23A H 0.7348 0.8816 0.5092 0.041 Uiso 1 1 calc R A .
H23B H 0.7419 0.6663 0.4984 0.041 Uiso 1 1 calc R . .
C24 C 0.72754(5) 0.7983(2) 0.36717(10) 0.0326(3) Uani 1 1 d . A .
H24A H 0.7080 0.9090 0.3422 0.039 Uiso 1 1 calc R . .
H24B H 0.7115 0.6927 0.3296 0.039 Uiso 1 1 calc R . .
C25 C 0.78534(5) 0.8165(2) 0.35088(10) 0.0339(4) Uani 1 1 d . . .
H25A H 0.8008 0.9257 0.3859 0.041 Uiso 1 1 calc R A .
H25B H 0.8052 0.7087 0.3791 0.041 Uiso 1 1 calc R . .
C26 C 0.79305(5) 0.8328(2) 0.24531(10) 0.0331(3) Uani 1 1 d . A .
H26A H 0.7771 0.7247 0.2101 0.040 Uiso 1 1 calc R . .
H26B H 0.7737 0.9418 0.2175 0.040 Uiso 1 1 calc R . .
C27 C 0.85070(5) 0.8477(2) 0.22875(10) 0.0342(4) Uani 1 1 d . . .
H27A H 0.8704 0.7409 0.2584 0.041 Uiso 1 1 calc R A .
H27B H 0.8664 0.9584 0.2618 0.041 Uiso 1 1 calc R . .
C28 C 0.85786(5) 0.8573(2) 0.12253(10) 0.0327(3) Uani 1 1 d . A .
H28A H 0.8415 0.7478 0.0893 0.039 Uiso 1 1 calc R . .
H28B H 0.8386 0.9654 0.0932 0.039 Uiso 1 1 calc R . .
C29 C 0.91548(5) 0.8690(2) 0.10501(10) 0.0359(4) Uani 1 1 d . . .
H29A H 0.9317 0.9801 0.1368 0.043 Uiso 1 1 calc R A .
H29B H 0.9350 0.7623 0.1353 0.043 Uiso 1 1 calc R . .
C30 C 0.92189(6) 0.8743(2) -0.00122(11) 0.0453(4) Uani 1 1 d . A .
H30A H 0.9092 0.7594 -0.0320 0.068 Uiso 1 1 calc R . .
H30B H 0.9594 0.8911 -0.0077 0.068 Uiso 1 1 calc R . .
H30C H 0.9012 0.9759 -0.0326 0.068 Uiso 1 1 calc R . .
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
C1 O1 C2 104.17(11) . .
C1 N1 C3 104.67(12) . .
C17 N2 C15 105.55(11) . .
C16 N3 C17 107.63(11) . .
C16 N3 C19 124.65(11) . .
C17 N3 C19 127.69(11) . .
N1 C1 O1 114.99(12) . .
N1 C1 C8 127.16(13) . .
O1 C1 C8 117.83(13) . .
C7 C2 O1 128.84(14) . .
C7 C2 C3 123.51(14) . .
O1 C2 C3 107.64(12) . .
C2 C3 C4 120.39(13) . .
C2 C3 N1 108.52(12) . .
C4 C3 N1 131.09(14) . .
C5 C4 C3 116.73(15) . .
C4 C5 C6 122.00(15) . .
C7 C6 C5 121.62(15) . .
C2 C7 C6 115.75(15) . .
C9 C8 C13 119.10(13) . .
C9 C8 C1 121.06(13) . .
C13 C8 C1 119.83(13) . .
C10 C9 C8 120.07(13) . .
C9 C10 C11 121.61(13) . .
C10 C11 C12 117.99(12) . .
C10 C11 C14 118.42(12) . .
C12 C11 C14 123.59(12) . .
C13 C12 C11 120.45(13) . .
C12 C13 C8 120.78(13) . .
C15 C14 C11 129.46(13) . .
C14 C15 N2 128.76(12) . .
C14 C15 C16 122.28(12) . .
N2 C15 C16 108.96(11) . .
O2 C16 N3 126.71(13) . .
O2 C16 C15 129.92(13) . .
N3 C16 C15 103.37(11) . .
N2 C17 N3 114.48(12) . .
N2 C17 C18 124.61(12) . .
N3 C17 C18 120.91(12) . .
N3 C19 C20 113.51(12) . .
C19 C20 C21 112.31(13) . .
C22 C21 C20 115.37(12) . .
C21 C22 C23 113.63(12) . .
C24 C23 C22 113.93(11) . .
C23 C24 C25 113.56(11) . .
C26 C25 C24 114.16(12) . .
C27 C26 C25 114.27(12) . .
C26 C27 C28 113.63(12) . .
C29 C28 C27 114.10(11) . .
C30 C29 C28 113.36(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3666(17) .
O1 C2 1.3823(17) .
N1 C1 1.2979(18) .
N1 C3 1.3997(17) .
O2 C16 1.2161(16) .
N2 C17 1.3014(17) .
N2 C15 1.3997(17) .
N3 C16 1.3835(18) .
N3 C17 1.3882(17) .
N3 C19 1.4598(17) .
C1 C8 1.456(2) .
C2 C7 1.374(2) .
C2 C3 1.384(2) .
C3 C4 1.386(2) .
C4 C5 1.380(2) .
C5 C6 1.389(2) .
C6 C7 1.382(2) .
C8 C9 1.390(2) .
C8 C13 1.3965(19) .
C9 C10 1.376(2) .
C10 C11 1.3996(19) .
C11 C12 1.4022(19) .
C11 C14 1.4522(19) .
C12 C13 1.3811(19) .
C14 C15 1.3471(19) .
C15 C16 1.4875(19) .
C17 C18 1.482(2) .
C19 C20 1.511(2) .
C20 C21 1.5269(19) .
C21 C22 1.517(2) .
C22 C23 1.5247(19) .
C23 C24 1.518(2) .
C24 C25 1.5250(18) .
C25 C26 1.5203(19) .
C26 C27 1.5203(18) .
C27 C28 1.5226(19) .
C28 C29 1.5217(18) .
C29 C30 1.517(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132604027
