#------------------------------------------------------------------------------
#$Date: 2024-04-06 04:30:31 +0300 (Sat, 06 Apr 2024) $
#$Revision: 291133 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248391.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_7248391
loop_
_publ_author_name
'Jin, Yuxin'
'Jiang, Bingli'
'Song, Huajian'
'Mei, Chanming'
'Liu, Zuoan'
'Zhang, Xiakai'
'Liu, Jinyuan'
'Gong, Yongyang'
_publ_section_title
;
 Monophenyl luminescent material with dual-state emission and pH
 sensitivity for cell imaging.
;
_journal_issue                   16
_journal_name_full               'RSC advances'
_journal_page_first              10942
_journal_page_last               10952
_journal_paper_doi               10.1039/d4ra01422g
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C22 H34 N4 O6'
_chemical_formula_sum            'C22 H36 N4 O6'
_chemical_formula_weight         452.55
_chemical_name_common            DMSS-AM
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-31 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.13(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.105(4)
_cell_length_b                   7.746(3)
_cell_length_c                   15.032(8)
_cell_measurement_reflns_used    323
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      33.13
_cell_measurement_theta_min      5.23
_cell_volume                     1176.4(9)
_computing_cell_refinement       'cis-12 2023.11.22'
_computing_data_reduction        'cis-12 2023.11.22'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.499
_diffrn_reflns_theta_min         5.227
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5692
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0863 after correction.
The Ratio of minimum to maximum transmission is 0.7558.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             488
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0701
_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)+(0.1368P)²+0.0191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1893
_refine_ls_wR_factor_ref         0.2109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1504
_reflns_number_total             2158
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra01422g2.cif
_cod_data_source_block           DMSS-AM
_cod_original_cell_volume        1176.5(9)
_cod_database_code               7248391
_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.
;
_olex2_refinement_description
;
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O001 O 0.33044(16) 0.1136(2) 0.56579(10) 0.0676(5) Uani 1 1 d . . . . .
O002 O 0.3751(2) 0.0722(2) 0.42328(12) 0.0765(6) Uani 1 1 d . . . . .
O003 O 0.4669(2) 1.1713(3) 0.87876(15) 0.0902(7) Uani 1 1 d . . . . .
N004 N 0.54607(19) 0.8380(2) 0.82218(13) 0.0604(5) Uani 1 1 d . . . . .
N005 N 0.5538(2) 0.6403(3) 0.66884(13) 0.0666(6) Uani 1 1 d . . . . .
C006 C 0.4421(2) 0.3366(3) 0.49304(15) 0.0537(6) Uani 1 1 d . . . . .
C007 C 0.4677(2) 0.4110(3) 0.57558(16) 0.0563(6) Uani 1 1 d . . . . .
C008 C 0.5253(2) 0.5744(3) 0.58595(15) 0.0558(6) Uani 1 1 d . . . . .
C009 C 0.3811(2) 0.1629(3) 0.48851(15) 0.0565(6) Uani 1 1 d . . . . .
C00A C 0.5759(3) 0.6536(3) 0.82808(18) 0.0694(7) Uani 1 1 d . . . . .
C00B C 0.5180(3) 0.5548(3) 0.74973(17) 0.0682(7) Uani 1 1 d . . . . .
C00C C 0.6288(3) 0.9417(4) 0.8812(2) 0.0769(8) Uani 1 1 d . . . . .
C00D C 0.2702(3) -0.0559(4) 0.5681(2) 0.0777(8) Uani 1 1 d . . . . .
C00E C 0.4085(3) 0.8786(4) 0.8394(3) 0.0834(9) Uani 1 1 d . . . . .
C00F C 0.6012(3) 1.1295(4) 0.8653(3) 0.0912(10) Uani 1 1 d . . . . .
C00G C 0.3844(4) 1.0671(5) 0.8244(3) 0.0958(11) Uani 1 1 d . . . . .
H007 H 0.449(2) 0.351(3) 0.6261(18) 0.060(7) Uiso 1 1 d . . . . .
H00E H 0.722(3) 0.910(4) 0.867(2) 0.086(9) Uiso 1 1 d . . . . .
H00C H 0.413(3) 0.541(4) 0.7526(19) 0.079(8) Uiso 1 1 d . . . . .
H00A H 0.542(3) 0.598(4) 0.884(2) 0.084(8) Uiso 1 1 d . . . . .
H00D H 0.557(3) 0.437(4) 0.7491(19) 0.077(8) Uiso 1 1 d . . . . .
H00B H 0.679(3) 0.646(3) 0.8272(16) 0.062(6) Uiso 1 1 d . . . . .
H00L H 0.616(3) 1.153(4) 0.800(3) 0.097(11) Uiso 1 1 d . . . . .
H00J H 0.386(4) 0.836(5) 0.904(3) 0.121(12) Uiso 1 1 d . . . . .
H00N H 0.290(4) 1.095(6) 0.838(3) 0.126(13) Uiso 1 1 d . . . . .
H00O H 0.408(4) 1.090(5) 0.762(3) 0.116(13) Uiso 1 1 d . . . . .
H00K H 0.352(3) 0.815(5) 0.798(3) 0.108(11) Uiso 1 1 d . . . . .
H00F H 0.611(4) 0.917(5) 0.948(3) 0.120(12) Uiso 1 1 d . . . . .
H00G H 0.184(5) -0.052(6) 0.531(3) 0.145(16) Uiso 1 1 d . . . . .
H005 H 0.570(3) 0.752(5) 0.674(2) 0.086(9) Uiso 1 1 d . . . . .
H00H H 0.225(4) -0.061(5) 0.624(3) 0.120(12) Uiso 1 1 d . . . . .
H00I H 0.325(4) -0.137(5) 0.540(3) 0.114(12) Uiso 1 1 d . . . . .
H00M H 0.651(4) 1.203(6) 0.910(3) 0.124(12) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C009 O001 C00D 116.7(2) . . ?
C00G O003 C00F 110.1(3) . . ?
C00C N004 C00A 112.8(2) . . ?
C00C N004 C00E 108.3(2) . . ?
C00E N004 C00A 113.4(2) . . ?
C008 N005 C00B 123.1(2) . . ?
C008 N005 H005 119(2) . . ?
C00B N005 H005 115(2) . . ?
C007 C006 C008 120.3(2) . 3_666 ?
C007 C006 C009 119.25(19) . . ?
C008 C006 C009 120.44(19) 3_666 . ?
C006 C007 C008 123.0(2) . . ?
C006 C007 H007 119.6(15) . . ?
C008 C007 H007 117.4(15) . . ?
N005 C008 C006 122.2(2) . 3_666 ?
N005 C008 C007 121.1(2) . . ?
C007 C008 C006 116.7(2) . 3_666 ?
O001 C009 C006 112.74(19) . . ?
O002 C009 O001 121.8(2) . . ?
O002 C009 C006 125.5(2) . . ?
N004 C00A C00B 111.8(2) . . ?
N004 C00A H00A 113.6(17) . . ?
N004 C00A H00B 104.9(13) . . ?
C00B C00A H00A 107.3(17) . . ?
C00B C00A H00B 109.5(13) . . ?
H00A C00A H00B 110(2) . . ?
N005 C00B C00A 109.0(2) . . ?
N005 C00B H00C 110.2(16) . . ?
N005 C00B H00D 108.1(16) . . ?
C00A C00B H00C 112.8(16) . . ?
C00A C00B H00D 109.0(17) . . ?
H00C C00B H00D 108(2) . . ?
N004 C00C C00F 109.6(3) . . ?
N004 C00C H00E 105.6(18) . . ?
N004 C00C H00F 112(2) . . ?
C00F C00C H00E 112.2(19) . . ?
C00F C00C H00F 107(2) . . ?
H00E C00C H00F 110(3) . . ?
O001 C00D H00G 108(3) . . ?
O001 C00D H00H 106(2) . . ?
O001 C00D H00I 110(2) . . ?
H00G C00D H00H 94(3) . . ?
H00G C00D H00I 106(4) . . ?
H00H C00D H00I 131(3) . . ?
N004 C00E C00G 109.7(3) . . ?
N004 C00E H00J 108(2) . . ?
N004 C00E H00K 109(2) . . ?
C00G C00E H00J 114(2) . . ?
C00G C00E H00K 108(2) . . ?
H00J C00E H00K 107(3) . . ?
O003 C00F C00C 112.1(3) . . ?
O003 C00F H00L 105(2) . . ?
O003 C00F H00M 104(2) . . ?
C00C C00F H00L 107(2) . . ?
C00C C00F H00M 111(2) . . ?
H00L C00F H00M 118(3) . . ?
O003 C00G C00E 112.3(3) . . ?
O003 C00G H00N 108(2) . . ?
O003 C00G H00O 107(2) . . ?
C00E C00G H00N 110(2) . . ?
C00E C00G H00O 106(2) . . ?
H00N C00G H00O 114(3) . . ?
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
O001 C009 1.334(3) . ?
O001 C00D 1.447(3) . ?
O002 C009 1.207(3) . ?
O003 C00F 1.414(4) . ?
O003 C00G 1.409(4) . ?
N004 C00A 1.462(3) . ?
N004 C00C 1.450(3) . ?
N004 C00E 1.454(4) . ?
N005 C008 1.372(3) . ?
N005 C00B 1.437(3) . ?
N005 H005 0.88(4) . ?
C006 C007 1.388(3) . ?
C006 C008 1.417(3) 3_666 ?
C006 C009 1.481(3) . ?
C007 C008 1.401(3) . ?
C007 H007 0.91(3) . ?
C00A C00B 1.513(4) . ?
C00A H00A 1.01(3) . ?
C00A H00B 1.04(3) . ?
C00B H00C 1.06(3) . ?
C00B H00D 0.99(3) . ?
C00C C00F 1.500(5) . ?
C00C H00E 1.00(3) . ?
C00C H00F 1.04(4) . ?
C00D H00G 1.03(5) . ?
C00D H00H 0.97(4) . ?
C00D H00I 0.94(4) . ?
C00E C00G 1.496(5) . ?
C00E H00J 1.06(4) . ?
C00E H00K 0.97(4) . ?
C00F H00L 1.00(4) . ?
C00F H00M 1.01(5) . ?
C00G H00N 1.00(4) . ?
C00G H00O 0.99(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N004 C00A C00B N005 49.8(3) . . . . ?
N004 C00C C00F O003 58.6(4) . . . . ?
N004 C00E C00G O003 -58.3(4) . . . . ?
C006 C007 C008 N005 -177.3(2) . . . . ?
C006 C007 C008 C006 -0.1(3) . . . 3_666 ?
C007 C006 C009 O001 14.1(3) . . . . ?
C007 C006 C009 O002 -166.2(2) . . . . ?
C008 N005 C00B C00A 174.5(2) . . . . ?
C008 C006 C007 C008 0.1(4) 3_666 . . . ?
C008 C006 C009 O001 -166.16(19) 3_666 . . . ?
C008 C006 C009 O002 13.5(3) 3_666 . . . ?
C009 C006 C007 C008 179.9(2) . . . . ?
C00A N004 C00C C00F 174.8(2) . . . . ?
C00A N004 C00E C00G -175.3(3) . . . . ?
C00B N005 C008 C006 178.0(2) . . . 3_666 ?
C00B N005 C008 C007 -4.9(4) . . . . ?
C00C N004 C00A C00B -163.9(2) . . . . ?
C00C N004 C00E C00G 58.7(4) . . . . ?
C00D O001 C009 O002 1.2(3) . . . . ?
C00D O001 C009 C006 -179.1(2) . . . . ?
C00E N004 C00A C00B 72.5(3) . . . . ?
C00E N004 C00C C00F -58.8(3) . . . . ?
C00F O003 C00G C00E 56.0(4) . . . . ?
C00G O003 C00F C00C -56.0(4) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 7.3 0.1 ?
2 0.500 0.500 0.000 7.3 0.1 ?
