#------------------------------------------------------------------------------
#$Date: 2022-01-18 10:41:21 +0200 (Tue, 18 Jan 2022) $
#$Revision: 272095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566006.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_1566006
loop_
_publ_author_name
'Yao, Guang-Xu'
'Zhang, Jin-Qiang'
'Li, Peng'
'Liu, Hui'
'Wang, Li'
'Sun, Yin-Xia'
'Dong, Wen-Kui'
_publ_section_title
;
 A unitary fluorescence probe to sense Co2+: Validated by theoretical
 studies and X-ray crystallography
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              120642
_journal_paper_doi               10.1016/j.ica.2021.120642
_journal_volume                  529
_journal_year                    2022
_chemical_formula_moiety         'C21 H20 N2 O5'
_chemical_formula_sum            'C21 H20 N2 O5'
_chemical_formula_weight         380.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 91.098(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.4132(18)
_cell_length_b                   4.9570(3)
_cell_length_c                   25.9948(12)
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.87
_cell_volume                     3660.5(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.060
_diffrn_reflns_theta_min         2.868
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0549
_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)+(0.0471P)²+3.1937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2731
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2022-529-120642.cif
_cod_data_source_block           11
_cod_database_code               1566006
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C14(H14),
 C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.59977(7) 0.3793(4) 0.76460(8) 0.0343(5) Uani 1 1 d . . . . .
C2 C 0.61715(7) 0.3963(4) 0.71522(8) 0.0323(5) Uani 1 1 d . . . . .
C3 C 0.65424(7) 0.2158(4) 0.70042(8) 0.0318(5) Uani 1 1 d . . . . .
C4 C 0.67249(8) 0.2054(5) 0.65016(9) 0.0394(5) Uani 1 1 d . . . . .
H4 H 0.660394 0.324320 0.624479 0.047 Uiso 1 1 calc R . . . .
C5 C 0.70731(8) 0.0266(5) 0.63794(9) 0.0446(6) Uani 1 1 d . . . . .
H5 H 0.718852 0.022779 0.603888 0.054 Uiso 1 1 calc R . . . .
C6 C 0.72614(8) -0.1508(5) 0.67493(9) 0.0442(6) Uani 1 1 d . . . . .
H6 H 0.750626 -0.271825 0.666138 0.053 Uiso 1 1 calc R . . . .
C7 C 0.70915(8) -0.1485(5) 0.72345(9) 0.0404(5) Uani 1 1 d . . . . .
H7 H 0.721734 -0.270326 0.748350 0.048 Uiso 1 1 calc R . . . .
C8 C 0.67315(7) 0.0317(4) 0.73748(8) 0.0334(5) Uani 1 1 d . . . . .
C9 C 0.65470(8) 0.0293(5) 0.78781(9) 0.0391(5) Uani 1 1 d . . . . .
H9 H 0.667393 -0.092188 0.812699 0.047 Uiso 1 1 calc R . . . .
C10 C 0.61922(8) 0.1977(5) 0.80106(9) 0.0395(5) Uani 1 1 d . . . . .
H10 H 0.607443 0.193264 0.835002 0.047 Uiso 1 1 calc R . . . .
C11 C 0.59877(7) 0.5948(4) 0.67898(8) 0.0338(5) Uani 1 1 d . . . . .
H11 H 0.613816 0.618366 0.646969 0.041 Uiso 1 1 calc R . . . .
C12 C 0.50914(7) 1.0587(5) 0.66120(8) 0.0359(5) Uani 1 1 d . . . . .
H12A H 0.513766 1.170047 0.692504 0.043 Uiso 1 1 calc R . . . .
H12B H 0.483487 0.928155 0.667356 0.043 Uiso 1 1 calc R . . . .
C13 C 0.49697(8) 1.2339(4) 0.61601(8) 0.0365(5) Uani 1 1 d . . . . .
H13A H 0.467592 1.333362 0.623151 0.044 Uiso 1 1 calc R . . . .
H13B H 0.522336 1.368382 0.611561 0.044 Uiso 1 1 calc R . . . .
C14 C 0.44629(8) 0.7652(5) 0.53329(8) 0.0379(5) Uani 1 1 d . . . . .
H14 H 0.468835 0.775710 0.506841 0.045 Uiso 1 1 calc R . . . .
C15 C 0.40757(8) 0.5763(4) 0.52827(8) 0.0355(5) Uani 1 1 d . . . . .
C16 C 0.37304(8) 0.5522(4) 0.56582(8) 0.0348(5) Uani 1 1 d . . . . .
C17 C 0.33675(8) 0.3651(4) 0.56062(8) 0.0357(5) Uani 1 1 d . . . . .
H17 H 0.313937 0.349025 0.586696 0.043 Uiso 1 1 calc R . . . .
C18 C 0.33395(8) 0.2032(4) 0.51762(8) 0.0353(5) Uani 1 1 d . . . . .
C19 C 0.36759(8) 0.2228(5) 0.47940(9) 0.0412(6) Uani 1 1 d . . . . .
H19 H 0.365625 0.111411 0.449702 0.049 Uiso 1 1 calc R . . . .
C20 C 0.40369(8) 0.4063(5) 0.48541(8) 0.0416(6) Uani 1 1 d . . . . .
H20 H 0.426775 0.417921 0.459539 0.050 Uiso 1 1 calc R . . . .
C21 C 0.26668(9) -0.0211(5) 0.55027(9) 0.0471(6) Uani 1 1 d . . . . .
H21A H 0.244248 -0.163689 0.540822 0.071 Uiso 1 1 calc GR . . . .
H21B H 0.249647 0.147886 0.555939 0.071 Uiso 1 1 calc GR . . . .
H21C H 0.283785 -0.072215 0.581886 0.071 Uiso 1 1 calc GR . . . .
N1 N 0.56275(6) 0.7386(4) 0.68923(7) 0.0358(4) Uani 1 1 d . . . . .
N2 N 0.45063(6) 0.9185(4) 0.57289(7) 0.0369(4) Uani 1 1 d . . . . .
O1 O 0.56355(5) 0.5321(3) 0.78133(6) 0.0437(4) Uani 1 1 d . . . . .
H1 H 0.553656 0.631327 0.757271 0.066 Uiso 1 1 calc GR . . . .
O2 O 0.55177(5) 0.9191(3) 0.64931(6) 0.0390(4) Uani 1 1 d . . . . .
O3 O 0.49075(5) 1.0852(3) 0.56909(5) 0.0408(4) Uani 1 1 d . . . . .
O4 O 0.37308(6) 0.7063(3) 0.60870(6) 0.0469(4) Uani 1 1 d . . . . .
H4A H 0.397046 0.805585 0.609263 0.070 Uiso 1 1 calc GR . . . .
O5 O 0.29930(5) 0.0150(3) 0.50970(6) 0.0429(4) 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
C2 C1 C10 121.2(2) . .
O1 C1 C2 123.3(2) . .
O1 C1 C10 115.49(19) . .
C1 C2 C3 119.0(2) . .
C1 C2 C11 120.77(19) . .
C3 C2 C11 120.22(18) . .
C4 C3 C2 123.5(2) . .
C4 C3 C8 117.4(2) . .
C8 C3 C2 119.05(19) . .
C3 C4 H4 119.5 . .
C5 C4 C3 121.1(2) . .
C5 C4 H4 119.5 . .
C4 C5 H5 119.5 . .
C4 C5 C6 121.0(2) . .
C6 C5 H5 119.5 . .
C5 C6 H6 120.2 . .
C7 C6 C5 119.6(2) . .
C7 C6 H6 120.2 . .
C6 C7 H7 119.4 . .
C6 C7 C8 121.1(2) . .
C8 C7 H7 119.4 . .
C7 C8 C3 119.8(2) . .
C7 C8 C9 121.0(2) . .
C9 C8 C3 119.2(2) . .
C8 C9 H9 119.4 . .
C10 C9 C8 121.2(2) . .
C10 C9 H9 119.4 . .
C1 C10 H10 119.9 . .
C9 C10 C1 120.3(2) . .
C9 C10 H10 119.9 . .
C2 C11 H11 119.3 . .
N1 C11 C2 121.43(19) . .
N1 C11 H11 119.3 . .
H12A C12 H12B 108.5 . .
C13 C12 H12A 110.3 . .
C13 C12 H12B 110.3 . .
O2 C12 H12A 110.3 . .
O2 C12 H12B 110.3 . .
O2 C12 C13 107.12(17) . .
C12 C13 H13A 109.0 . .
C12 C13 H13B 109.0 . .
H13A C13 H13B 107.8 . .
O3 C13 C12 113.10(18) . .
O3 C13 H13A 109.0 . .
O3 C13 H13B 109.0 . .
C15 C14 H14 119.5 . .
N2 C14 H14 119.5 . .
N2 C14 C15 121.1(2) . .
C16 C15 C14 122.2(2) . .
C20 C15 C14 120.6(2) . .
C20 C15 C16 117.2(2) . .
C17 C16 C15 121.1(2) . .
O4 C16 C15 122.4(2) . .
O4 C16 C17 116.48(19) . .
C16 C17 H17 120.1 . .
C18 C17 C16 119.9(2) . .
C18 C17 H17 120.1 . .
C17 C18 C19 120.5(2) . .
O5 C18 C17 123.3(2) . .
O5 C18 C19 116.16(19) . .
C18 C19 H19 120.5 . .
C20 C19 C18 119.0(2) . .
C20 C19 H19 120.5 . .
C15 C20 H20 118.8 . .
C19 C20 C15 122.3(2) . .
C19 C20 H20 118.8 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O5 C21 H21A 109.5 . .
O5 C21 H21B 109.5 . .
O5 C21 H21C 109.5 . .
C11 N1 O2 111.67(17) . .
C14 N2 O3 110.83(17) . .
C1 O1 H1 109.5 . .
N1 O2 C12 109.01(15) . .
N2 O3 C13 109.14(15) . .
C16 O4 H4A 109.5 . .
C18 O5 C21 116.68(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.387(3) .
C1 C10 1.412(3) .
C1 O1 1.356(2) .
C2 C3 1.440(3) .
C2 C11 1.452(3) .
C3 C4 1.416(3) .
C3 C8 1.425(3) .
C4 H4 0.9500 .
C4 C5 1.370(3) .
C5 H5 0.9500 .
C5 C6 1.401(3) .
C6 H6 0.9500 .
C6 C7 1.359(3) .
C7 H7 0.9500 .
C7 C8 1.411(3) .
C8 C9 1.419(3) .
C9 H9 0.9500 .
C9 C10 1.358(3) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C11 N1 1.279(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C12 C13 1.496(3) .
C12 O2 1.434(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 O3 1.433(2) .
C14 H14 0.9500 .
C14 C15 1.448(3) .
C14 N2 1.284(3) .
C15 C16 1.402(3) .
C15 C20 1.400(3) .
C16 C17 1.392(3) .
C16 O4 1.351(2) .
C17 H17 0.9500 .
C17 C18 1.377(3) .
C18 C19 1.395(3) .
C18 O5 1.369(3) .
C19 H19 0.9500 .
C19 C20 1.378(3) .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C21 O5 1.428(3) .
N1 O2 1.401(2) .
N2 O3 1.413(2) .
O1 H1 0.8400 .
O4 H4A 0.8400 .
