#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/80/7128037.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_7128037
loop_
_publ_author_name
'Liu, Huijing'
'Zhang, Sisi'
'Ding, Liping'
'Fang, Yu'
_publ_section_title
;
 Dual-state efficient chromophore with pH-responsive and
 solvatofluorochromic properties based on an asymmetric single benzene
 framework.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4011
_journal_page_last               4014
_journal_paper_doi               10.1039/d1cc00718a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C15 H22 N2 O4'
_chemical_formula_weight         294.34
_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
;
2021-02-05 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4663(5)
_cell_length_b                   7.8880(2)
_cell_length_c                   10.6546(3)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      53.84
_cell_measurement_theta_min      3.49
_cell_volume                     1549.71(7)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      210(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12000
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.860
_diffrn_reflns_theta_min         2.084
_exptl_absorpt_coefficient_mu    0.481
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0356
_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)+(0.0755P)²+0.3554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2524
_reflns_number_total             2815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc00718a2.cif
_cod_data_source_block           11_a
_cod_depositor_comments          'Adding full bibliography for 7128037.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128037
_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   0.945
_shelx_estimated_absorpt_t_max   0.958
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
C1 C 0.56665(8) 0.3621(2) 0.22253(16) 0.0599(4) Uani 1 1 d . . . . .
H1A H 0.543393 0.311337 0.147848 0.090 Uiso 1 1 calc R U . . .
H1B H 0.615588 0.318261 0.234999 0.090 Uiso 1 1 calc R U . . .
H1C H 0.568370 0.484187 0.212297 0.090 Uiso 1 1 calc R U . . .
C2 C 0.52482(6) 0.32006(18) 0.33309(13) 0.0429(3) Uani 1 1 d . . . . .
H2A H 0.525266 0.197385 0.347657 0.051 Uiso 1 1 calc R U . . .
H2B H 0.546067 0.376337 0.408372 0.051 Uiso 1 1 calc R U . . .
C3 C 0.40518(6) 0.36400(15) 0.39812(11) 0.0345(3) Uani 1 1 d . . . . .
C4 C 0.33181(6) 0.42846(14) 0.36154(11) 0.0308(3) Uani 1 1 d . . . . .
C5 C 0.27794(6) 0.43794(15) 0.45056(11) 0.0321(3) Uani 1 1 d . . . . .
C6 C 0.20936(6) 0.49885(15) 0.40735(11) 0.0325(3) Uani 1 1 d . . . . .
H6 H 0.171922 0.503020 0.463646 0.039 Uiso 1 1 calc R U . . .
C7 C 0.19517(6) 0.55282(14) 0.28475(11) 0.0300(3) Uani 1 1 d . . . . .
C8 C 0.24896(6) 0.54379(14) 0.19513(10) 0.0295(3) Uani 1 1 d . . . . .
C9 C 0.31599(6) 0.48010(14) 0.23730(10) 0.0308(3) Uani 1 1 d . . . . .
H9 H 0.352573 0.471180 0.179633 0.037 Uiso 1 1 calc R U . . .
C10 C 0.17641(7) 0.51039(18) -0.00092(12) 0.0419(3) Uani 1 1 d . . . . .
H10A H 0.191540 0.395420 -0.018448 0.063 Uiso 1 1 calc R U . . .
H10B H 0.165122 0.569390 -0.079427 0.063 Uiso 1 1 calc R U . . .
H10C H 0.133715 0.507559 0.048223 0.063 Uiso 1 1 calc R U . . .
C11 C 0.29776(7) 0.61567(18) -0.00567(12) 0.0404(3) Uani 1 1 d . . . . .
H11A H 0.333847 0.686181 0.038494 0.061 Uiso 1 1 calc R U . . .
H11B H 0.283303 0.667610 -0.085652 0.061 Uiso 1 1 calc R U . . .
H11C H 0.318135 0.504465 -0.020109 0.061 Uiso 1 1 calc R U . . .
C12 C 0.12292(6) 0.63432(15) 0.25677(10) 0.0313(3) Uani 1 1 d . . . . .
C13 C -0.00245(6) 0.61923(18) 0.29796(14) 0.0460(3) Uani 1 1 d . . . . .
H13A H -0.039325 0.529779 0.293607 0.055 Uiso 1 1 calc R U . . .
H13B H -0.009050 0.689112 0.222153 0.055 Uiso 1 1 calc R U . . .
C14 C -0.01185(9) 0.7262(2) 0.41136(16) 0.0604(4) Uani 1 1 d . . . . .
H14A H 0.000621 0.660580 0.486439 0.091 Uiso 1 1 calc R U . . .
H14B H -0.061905 0.763147 0.412574 0.091 Uiso 1 1 calc R U . . .
H14C H 0.019634 0.824447 0.408833 0.091 Uiso 1 1 calc R U . . .
C15 C 0.23908(8) 0.41915(19) 0.66838(12) 0.0460(3) Uani 1 1 d . . . . .
H15A H 0.224675 0.537395 0.668749 0.069 Uiso 1 1 calc R U . . .
H15B H 0.261101 0.389073 0.750066 0.069 Uiso 1 1 calc R U . . .
H15C H 0.196749 0.348713 0.650212 0.069 Uiso 1 1 calc R U . . .
N1 N 0.29059(6) 0.39282(15) 0.57359(10) 0.0420(3) Uani 1 1 d . . . . .
H1 H 0.335339 0.348444 0.593476 0.050 Uiso 1 1 d R U . . .
N2 N 0.23488(5) 0.59883(13) 0.06961(9) 0.0332(2) Uani 1 1 d . . . . .
O1 O 0.45107(4) 0.37896(12) 0.30608(8) 0.0423(2) Uani 1 1 d . . . . .
O2 O 0.42337(5) 0.30356(14) 0.49975(9) 0.0510(3) Uani 1 1 d . . . . .
O3 O 0.11371(5) 0.76744(12) 0.20330(9) 0.0443(3) Uani 1 1 d . . . . .
O4 O 0.06945(4) 0.54306(11) 0.30290(9) 0.0407(2) 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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 107.13(11) . . ?
O1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 122.27(11) . . ?
O2 C3 C4 125.12(11) . . ?
O1 C3 C4 112.61(10) . . ?
C9 C4 C5 120.03(10) . . ?
C9 C4 C3 119.36(10) . . ?
C5 C4 C3 120.61(10) . . ?
N1 C5 C6 120.45(10) . . ?
N1 C5 C4 122.69(11) . . ?
C6 C5 C4 116.86(10) . . ?
C7 C6 C5 122.29(10) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 121.08(10) . . ?
C6 C7 C12 116.18(10) . . ?
C8 C7 C12 122.52(10) . . ?
C9 C8 C7 116.46(10) . . ?
C9 C8 N2 122.12(10) . . ?
C7 C8 N2 121.41(10) . . ?
C8 C9 C4 123.24(10) . . ?
C8 C9 H9 118.4 . . ?
C4 C9 H9 118.4 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 123.78(11) . . ?
O3 C12 C7 124.85(10) . . ?
O4 C12 C7 111.33(10) . . ?
O4 C13 C14 110.48(12) . . ?
O4 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O4 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 N1 C15 123.39(10) . . ?
C5 N1 H1 115.4 . . ?
C15 N1 H1 121.2 . . ?
C8 N2 C11 115.96(9) . . ?
C8 N2 C10 115.64(9) . . ?
C11 N2 C10 110.53(10) . . ?
C3 O1 C2 116.84(9) . . ?
C12 O4 C13 117.05(10) . . ?
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
C1 C2 1.481(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 O1 1.4531(14) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 O2 1.2139(15) . ?
C3 O1 1.3353(15) . ?
C3 C4 1.4796(16) . ?
C4 C9 1.4007(16) . ?
C4 C5 1.4131(16) . ?
C5 N1 1.3662(15) . ?
C5 C6 1.4084(16) . ?
C6 C7 1.3854(16) . ?
C6 H6 0.9400 . ?
C7 C8 1.4164(15) . ?
C7 C12 1.4963(15) . ?
C8 C9 1.3879(16) . ?
C8 N2 1.4167(14) . ?
C9 H9 0.9400 . ?
C10 N2 1.4593(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 N2 1.4525(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 O3 1.2024(15) . ?
C12 O4 1.3368(14) . ?
C13 O4 1.4557(14) . ?
C13 C14 1.492(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 N1 1.4393(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
N1 H1 0.9117 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352609
