#------------------------------------------------------------------------------
#$Date: 2023-06-05 08:00:26 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284340 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246661.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_7246661
loop_
_publ_author_name
'Ke, Hao-Wei'
'Sung, Kuangsen'
_publ_section_title
;
 7-membered-ring effect on fluorescence quantum yield: does
 metal-complexation-induced twisting-inhibition of an amino GFP
 chromophore derivative enhance fluorescence?
;
_journal_issue                   20
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              14627
_journal_page_last               14634
_journal_paper_doi               10.1039/d3cp00467h
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C18 H18 N6 O7 Zn'
_chemical_formula_weight         495.77
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-10-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.778(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1168(9)
_cell_length_b                   14.3578(11)
_cell_length_c                   11.4115(8)
_cell_measurement_temperature    100(2)
_cell_volume                     1951.3(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_min         2.424
_exptl_absorpt_coefficient_mu    1.317
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0310
_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)+(0.0312P)²+1.9349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4398
_reflns_number_total             4870
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp00467h2.cif
_cod_data_source_block           21JUL48
_cod_depositor_comments
'Adding full bibliography for 7246661--7246662.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246661
_shelx_shelxl_version_number     2018/3
_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   0.677
_shelx_estimated_absorpt_t_max   0.916
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
Zn1 Zn 0.73644(2) 0.17543(2) 0.45962(2) 0.01693(7) Uani 1 1 d . . . . .
O1 O 1.10870(12) 0.18083(10) 0.35596(15) 0.0301(3) Uani 1 1 d . . . . .
O2 O 0.80587(15) 0.05142(12) 0.57189(14) 0.0427(4) Uani 1 1 d . . . . .
O3 O 0.89530(12) 0.03590(10) 0.77899(13) 0.0275(3) Uani 1 1 d . . . . .
O4 O 0.8360(2) 0.16996(12) 0.69128(19) 0.0626(6) Uani 1 1 d . . . . .
O5 O 0.69696(11) 0.29849(9) 0.53231(12) 0.0245(3) Uani 1 1 d . . . . .
O6 O 0.63399(14) 0.33066(11) 0.32928(14) 0.0361(3) Uani 1 1 d . . . . .
O7 O 0.62863(13) 0.43542(10) 0.46433(14) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.57134(13) 0.13474(10) 0.41878(15) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.67860(12) 0.11400(10) 0.26397(14) 0.0167(3) Uani 1 1 d . . . . .
H2A H 0.708165 0.146912 0.226533 0.020 Uiso 1 1 d . U . . .
N3 N 0.88331(12) 0.20844(10) 0.44467(14) 0.0188(3) Uani 1 1 d . . . . .
N4 N 1.03956(13) 0.28230(11) 0.46253(15) 0.0225(3) Uani 1 1 d . . . . .
N5 N 0.84775(12) 0.08574(11) 0.68397(15) 0.0223(3) Uani 1 1 d . . . . .
N6 N 0.65140(13) 0.35711(12) 0.43948(15) 0.0251(3) Uani 1 1 d . . . . .
C1 C 0.52799(17) 0.13057(13) 0.50685(19) 0.0258(4) Uani 1 1 d . . . . .
H1 H 0.575902 0.140963 0.595194 0.031 Uiso 1 1 calc R U . . .
C2 C 0.41563(18) 0.11157(13) 0.4722(2) 0.0301(4) Uani 1 1 d . . . . .
H2 H 0.386360 0.110636 0.535516 0.036 Uiso 1 1 calc R U . . .
C3 C 0.34672(17) 0.09399(13) 0.3444(2) 0.0297(4) Uani 1 1 d . . . . .
H3 H 0.269364 0.080596 0.318524 0.036 Uiso 1 1 calc R U . . .
C4 C 0.39184(15) 0.09614(13) 0.2543(2) 0.0257(4) Uani 1 1 d . . . . .
H4 H 0.346428 0.082532 0.166208 0.031 Uiso 1 1 calc R U . . .
C5 C 0.50450(14) 0.11851(12) 0.29488(17) 0.0199(3) Uani 1 1 d . . . . .
C6 C 0.55684(14) 0.13010(12) 0.20042(17) 0.0198(3) Uani 1 1 d . . . . .
H6A H 0.522209 0.085436 0.128398 0.024 Uiso 1 1 calc R U . . .
H6B H 0.542085 0.193853 0.164069 0.024 Uiso 1 1 calc R U . . .
C7 C 0.71300(14) 0.01830(12) 0.27242(15) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.63570(15) -0.05370(12) 0.24573(17) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.559522 -0.039846 0.226550 0.025 Uiso 1 1 calc R U . . .
C9 C 0.66875(16) -0.14583(13) 0.24682(18) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.615128 -0.194406 0.228956 0.029 Uiso 1 1 calc R U . . .
C10 C 0.77881(17) -0.16718(13) 0.27364(19) 0.0250(4) Uani 1 1 d . . . . .
H10 H 0.801117 -0.230026 0.272703 0.030 Uiso 1 1 calc R U . . .
C11 C 0.85623(15) -0.09575(12) 0.30192(17) 0.0213(3) Uani 1 1 d . . . . .
H11 H 0.931877 -0.110514 0.319576 0.026 Uiso 1 1 calc R U . . .
C12 C 0.82675(14) -0.00231(12) 0.30538(16) 0.0173(3) Uani 1 1 d . . . . .
C13 C 0.91627(14) 0.06580(12) 0.33398(16) 0.0188(3) Uani 1 1 d . . . . .
H13 H 0.973566 0.044681 0.310115 0.023 Uiso 1 1 calc R U . . .
C14 C 0.93696(14) 0.15147(12) 0.38614(16) 0.0192(3) Uani 1 1 d . . . . .
C15 C 1.03967(15) 0.20168(13) 0.39568(18) 0.0223(3) Uani 1 1 d . . . . .
C16 C 0.94643(15) 0.28313(13) 0.48710(16) 0.0206(3) Uani 1 1 d . . . . .
C17 C 1.12315(16) 0.35551(14) 0.4919(2) 0.0277(4) Uani 1 1 d . . . . .
H17A H 1.147386 0.375310 0.581726 0.042 Uiso 1 1 calc R U . . .
H17B H 1.090510 0.408663 0.434400 0.042 Uiso 1 1 calc R U . . .
H17C H 1.187944 0.331922 0.479218 0.042 Uiso 1 1 calc R U . . .
C18 C 0.92444(17) 0.36287(14) 0.55444(19) 0.0274(4) Uani 1 1 d . . . . .
H18A H 0.890320 0.413554 0.492843 0.041 Uiso 1 1 calc R U . . .
H18B H 0.995264 0.384366 0.622917 0.041 Uiso 1 1 calc R U . . .
H18C H 0.873113 0.343720 0.592371 0.041 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'
Zn Zn 0.2839 1.4301 '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
_geom_angle_publ_flag
N3 Zn1 N1 163.74(6) . . ?
N3 Zn1 O5 103.45(6) . . ?
N1 Zn1 O5 85.40(5) . . ?
N3 Zn1 O2 93.58(6) . . ?
N1 Zn1 O2 92.38(6) . . ?
O5 Zn1 O2 124.75(6) . . ?
N3 Zn1 N2 86.87(5) . . ?
N1 Zn1 N2 77.28(5) . . ?
O5 Zn1 N2 133.88(5) . . ?
O2 Zn1 N2 98.66(6) . . ?
N3 Zn1 O4 90.15(7) . . ?
N1 Zn1 O4 105.61(7) . . ?
O5 Zn1 O4 72.85(5) . . ?
O2 Zn1 O4 54.71(6) . . ?
N2 Zn1 O4 152.99(5) . . ?
N5 O2 Zn1 100.12(12) . . ?
N5 O4 Zn1 89.04(13) . . ?
N6 O5 Zn1 109.29(10) . . ?
C5 N1 C1 119.14(16) . . ?
C5 N1 Zn1 116.25(11) . . ?
C1 N1 Zn1 124.44(13) . . ?
C7 N2 C6 115.43(14) . . ?
C7 N2 Zn1 110.33(10) . . ?
C6 N2 Zn1 106.07(10) . . ?
C7 N2 H2A 112.1 . . ?
C6 N2 H2A 107.5 . . ?
Zn1 N2 H2A 104.7 . . ?
C16 N3 C14 106.48(14) . . ?
C16 N3 Zn1 128.52(12) . . ?
C14 N3 Zn1 124.99(12) . . ?
C16 N4 C15 109.16(15) . . ?
C16 N4 C17 126.94(16) . . ?
C15 N4 C17 123.77(16) . . ?
O4 N5 O3 123.09(18) . . ?
O4 N5 O2 116.13(17) . . ?
O3 N5 O2 120.77(17) . . ?
O7 N6 O6 123.78(17) . . ?
O7 N6 O5 118.89(15) . . ?
O6 N6 O5 117.33(16) . . ?
N1 C1 C2 121.83(19) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.08(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.08(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.96(19) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.87(17) . . ?
N1 C5 C6 116.32(15) . . ?
C4 C5 C6 121.76(17) . . ?
N2 C6 C5 110.82(14) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C12 119.75(15) . . ?
C8 C7 N2 121.13(15) . . ?
C12 C7 N2 119.11(15) . . ?
C7 C8 C9 120.64(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.47(17) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.01(17) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 122.16(17) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C7 117.87(15) . . ?
C11 C12 C13 116.31(15) . . ?
C7 C12 C13 125.67(15) . . ?
C14 C13 C12 135.09(16) . . ?
C14 C13 H13 112.5 . . ?
C12 C13 H13 112.5 . . ?
C13 C14 N3 133.61(16) . . ?
C13 C14 C15 118.91(16) . . ?
N3 C14 C15 107.39(15) . . ?
O1 C15 N4 125.96(17) . . ?
O1 C15 C14 130.48(17) . . ?
N4 C15 C14 103.56(15) . . ?
N3 C16 N4 113.37(16) . . ?
N3 C16 C18 126.47(16) . . ?
N4 C16 C18 120.16(16) . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N3 2.0592(14) . ?
Zn1 N1 2.0982(15) . ?
Zn1 O5 2.1066(13) . ?
Zn1 O2 2.1594(17) . ?
Zn1 N2 2.2178(14) . ?
Zn1 O4 2.410(2) . ?
O1 C15 1.208(2) . ?
O2 N5 1.262(2) . ?
O3 N5 1.2288(19) . ?
O4 N5 1.226(2) . ?
O5 N6 1.287(2) . ?
O6 N6 1.240(2) . ?
O7 N6 1.227(2) . ?
N1 C5 1.335(2) . ?
N1 C1 1.348(2) . ?
N2 C7 1.437(2) . ?
N2 C6 1.469(2) . ?
N2 H2A 0.8337 . ?
N3 C16 1.317(2) . ?
N3 C14 1.416(2) . ?
N4 C16 1.363(2) . ?
N4 C15 1.387(2) . ?
N4 C17 1.453(2) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.510(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.389(2) . ?
C7 C12 1.409(2) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.456(2) . ?
C13 C14 1.344(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.491(2) . ?
C16 C18 1.473(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
