#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234632.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_7234632
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            'C22 H21 N3 O2'
_chemical_formula_weight         359.42
_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                 101.338(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6778(5)
_cell_length_b                   34.671(4)
_cell_length_c                   11.6713(16)
_cell_measurement_reflns_used    1069
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      18.85
_cell_measurement_theta_min      2.35
_cell_volume                     1856.0(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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayers optics'
_diffrn_radiation_source         micro-focus
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1354
_diffrn_reflns_av_sigmaI/netI    0.1251
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29993
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         5.12
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1597
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0698P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                1706
_reflns_number_total             3626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-2793.cif
_cod_data_source_block           2
_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               7234632
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
C1 C -0.1321(6) 0.52699(8) 0.2598(3) 0.0420(7) Uani 1 1 d . . .
N1 N -0.2471(4) 0.51550(6) 0.34743(17) 0.0399(8) Uani 0.67(3) 1 d P A 1
O1 O -0.2222(4) 0.50703(6) 0.15974(17) 0.0422(8) Uani 0.67(3) 1 d P A 1
N1' N -0.2222(4) 0.50703(6) 0.15974(17) 0.0422(8) Uani 0.33(3) 1 d P A 2
O1' O -0.2471(4) 0.51550(6) 0.34743(17) 0.0399(8) Uani 0.33(3) 1 d P A 2
N2 N 0.7665(5) 0.66179(6) 0.08504(18) 0.0401(6) Uani 1 1 d . A .
N3 N 1.0999(5) 0.70916(6) 0.13417(18) 0.0368(6) Uani 1 1 d . A .
O2 O 1.1173(4) 0.71473(5) 0.33289(17) 0.0504(6) Uani 1 1 d . . .
C2 C -0.4309(5) 0.48516(8) 0.3035(2) 0.0364(7) Uani 1 1 d . . .
C3 C -0.4143(5) 0.47986(8) 0.1879(2) 0.0385(7) Uani 1 1 d . A .
C4 C -0.5701(6) 0.45207(9) 0.1193(2) 0.0488(8) Uani 1 1 d . . .
H4 H -0.5568 0.4486 0.0398 0.059 Uiso 1 1 calc R A .
C5 C -0.7487(6) 0.42920(9) 0.1730(3) 0.0545(8) Uani 1 1 d . A .
H5 H -0.8590 0.4092 0.1294 0.065 Uiso 1 1 calc R . .
C6 C -0.7701(6) 0.43480(9) 0.2885(3) 0.0505(8) Uani 1 1 d . . .
H6 H -0.8977 0.4188 0.3215 0.061 Uiso 1 1 calc R A .
C7 C -0.6121(6) 0.46278(8) 0.3566(2) 0.0446(7) Uani 1 1 d . A .
H7 H -0.6266 0.4665 0.4359 0.054 Uiso 1 1 calc R . .
C8 C 0.0756(5) 0.55800(7) 0.2632(2) 0.0353(7) Uani 1 1 d . A .
C9 C 0.1714(5) 0.56994(8) 0.1636(2) 0.0382(7) Uani 1 1 d . . .
H9 H 0.1018 0.5572 0.0915 0.046 Uiso 1 1 calc R A .
C10 C 0.3658(5) 0.59997(8) 0.1677(2) 0.0383(7) Uani 1 1 d . A .
H10 H 0.4259 0.6081 0.0984 0.046 Uiso 1 1 calc R . .
C11 C 0.4756(5) 0.61868(7) 0.2738(2) 0.0327(6) Uani 1 1 d . . .
C12 C 0.3815(5) 0.60578(8) 0.3734(2) 0.0378(7) Uani 1 1 d . A .
H12 H 0.4568 0.6177 0.4463 0.045 Uiso 1 1 calc R . .
C13 C 0.1831(5) 0.57630(8) 0.3690(2) 0.0388(7) Uani 1 1 d . . .
H13 H 0.1197 0.5685 0.4379 0.047 Uiso 1 1 calc R A .
C14 C 0.6842(5) 0.65024(7) 0.2860(2) 0.0362(7) Uani 1 1 d . A .
H14 H 0.7428 0.6597 0.3634 0.043 Uiso 1 1 calc R . .
C15 C 0.8078(5) 0.66820(7) 0.2064(2) 0.0335(6) Uani 1 1 d . . .
C16 C 1.0231(6) 0.69962(8) 0.2386(3) 0.0377(7) Uani 1 1 d . A .
C17 C 0.9408(6) 0.68599(8) 0.0482(2) 0.0428(7) Uani 1 1 d . . .
C18 C 0.9791(8) 0.68852(9) -0.0747(2) 0.0658(10) Uani 1 1 d . A .
H18A H 0.8348 0.6721 -0.1240 0.099 Uiso 1 1 calc R . .
H18B H 1.1758 0.6799 -0.0797 0.099 Uiso 1 1 calc R . .
H18C H 0.9522 0.7153 -0.1016 0.099 Uiso 1 1 calc R . .
C19 C 1.2909(5) 0.74142(7) 0.1218(2) 0.0402(7) Uani 1 1 d . . .
H19A H 1.3646 0.7384 0.0484 0.048 Uiso 1 1 calc R A .
H19B H 1.4606 0.7411 0.1876 0.048 Uiso 1 1 calc R . .
C20 C 1.1364(5) 0.77952(7) 0.1201(2) 0.0374(7) Uani 1 1 d . A .
H20A H 1.0424 0.7810 0.1889 0.045 Uiso 1 1 calc R . .
H20B H 0.9807 0.7808 0.0492 0.045 Uiso 1 1 calc R . .
C21 C 1.3374(6) 0.81387(8) 0.1213(2) 0.0438(7) Uani 1 1 d . . .
H21A H 1.5070 0.8108 0.1863 0.053 Uiso 1 1 calc R A .
H21B H 1.4112 0.8143 0.0474 0.053 Uiso 1 1 calc R . .
C22 C 1.1899(6) 0.85192(8) 0.1351(2) 0.0500(8) Uani 1 1 d . A .
H22A H 1.0298 0.8560 0.0682 0.075 Uiso 1 1 calc R . .
H22B H 1.3317 0.8729 0.1388 0.075 Uiso 1 1 calc R . .
H22C H 1.1125 0.8515 0.2073 0.075 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
N1 C1 O1 114.4(2) . .
N1 C1 C8 125.7(3) . .
O1 C1 C8 119.9(2) . .
C1 N1 C2 105.2(2) . .
C1 O1 C3 104.5(2) . .
C17 N2 C15 105.0(2) . .
C16 N3 C17 107.8(2) . .
C16 N3 C19 123.0(2) . .
C17 N3 C19 128.9(2) . .
C3 C2 C7 121.4(3) . .
C3 C2 N1 108.2(2) . .
C7 C2 N1 130.4(3) . .
C4 C3 C2 122.7(3) . .
C4 C3 O1 129.5(2) . .
C2 C3 O1 107.8(2) . .
C3 C4 C5 115.9(3) . .
C6 C5 C4 121.6(3) . .
C7 C6 C5 121.9(3) . .
C6 C7 C2 116.3(3) . .
C9 C8 C13 119.1(2) . .
C9 C8 C1 121.7(3) . .
C13 C8 C1 119.2(2) . .
C10 C9 C8 121.0(2) . .
C9 C10 C11 120.4(2) . .
C12 C11 C10 117.8(2) . .
C12 C11 C14 118.4(2) . .
C10 C11 C14 123.8(2) . .
C13 C12 C11 121.9(2) . .
C12 C13 C8 119.7(2) . .
C15 C14 C11 130.9(2) . .
C14 C15 N2 129.1(2) . .
C14 C15 C16 122.0(2) . .
N2 C15 C16 108.9(2) . .
O2 C16 N3 125.8(3) . .
O2 C16 C15 130.7(2) . .
N3 C16 C15 103.6(2) . .
N2 C17 N3 114.7(2) . .
N2 C17 C18 124.1(3) . .
N3 C17 C18 121.1(2) . .
N3 C19 C20 111.9(2) . .
C19 C20 C21 113.2(2) . .
C22 C21 C20 113.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.308(3) .
C1 O1 1.352(3) .
C1 C8 1.444(4) .
N1 C2 1.391(3) .
O1 C3 1.385(3) .
N2 C17 1.300(3) .
N2 C15 1.409(3) .
N3 C16 1.377(3) .
N3 C17 1.383(3) .
N3 C19 1.456(3) .
O2 C16 1.220(3) .
C2 C3 1.379(3) .
C2 C7 1.383(4) .
C3 C4 1.368(4) .
C4 C5 1.387(4) .
C5 C6 1.385(4) .
C6 C7 1.374(4) .
C8 C9 1.389(3) .
C8 C13 1.391(3) .
C9 C10 1.377(4) .
C10 C11 1.403(3) .
C11 C12 1.394(3) .
C11 C14 1.455(4) .
C12 C13 1.375(4) .
C14 C15 1.340(3) .
C15 C16 1.481(4) .
C17 C18 1.483(4) .
C19 C20 1.504(3) .
C20 C21 1.516(4) .
C21 C22 1.512(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132604026
