Multiple stimulus modulated organic crystal polymorphs with tunable luminescence behavior
Zhou, Qian; Feng, Mingxia; Shi, Caihong; Qian, Mengqiu; Ma, Xiurong; He, Runying; Meng, Xian; Shi, Yonggang; Cao, Qiue; Zheng, Liyan; Chemical Science 16 (2025) 9988–9997; doi:10.1039/D5SC01503K

data_1574583
_publ_section_title
;
 Multiple stimulus modulated organic crystal polymorphs with tunable
 luminescence behavior
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9988
_journal_page_last               9997
_journal_paper_doi               10.1039/D5SC01503K
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C52 H37 N3, 2(Br), 3(H2 O), C H4 O'
_chemical_formula_sum            'C53 H47 Br2 N3 O4'
_chemical_formula_weight         949.75
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-01-24 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.967(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.3843(11)
_cell_length_b                   7.1312(2)
_cell_length_c                   33.4701(7)
_cell_measurement_reflns_used    6737
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4050
_cell_measurement_theta_min      2.3180
_cell_volume                     9073.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -73.00  -2.00   0.50    0.31    --  -39.45  98.00 108.00  142
  2  \w    -68.00 -43.00   0.50    0.31    --  -52.00  98.00 108.00   50
  3  \w    -44.00  41.00   0.50    0.31    --  -39.45  37.00-120.00  170
  4  \w    -10.00  82.00   0.50    0.31    --   39.45 -98.00   0.00  184
  5  \w     33.00  84.00   0.50    1.24    --  111.82 -94.00  90.00  102
  6  \w     49.00 100.00   0.50    1.24    --  111.82 -94.00  60.00  102
  7  \w     57.00 104.00   0.50    1.24    --  111.82 -98.00   0.00   94
  8  \w     67.00  95.00   0.50    1.24    --  111.82 -77.00   0.00   56
  9  \w     38.00  66.00   0.50    1.24    --  111.82 -61.00 120.00   56
 10  \w     42.00  67.00   0.50    1.24    --  111.82 -61.00  60.00   50
 11  \w     38.00  66.00   0.50    1.24    --  111.82 -61.00  30.00   56
 12  \w     38.00  64.00   0.50    1.24    --  111.82 -61.00 -30.00   52
 13  \w     39.00  68.00   0.50    1.24    --  111.82 -61.00-180.00   58
 14  \w     41.00  66.00   0.50    1.24    --  111.82 -61.00-150.00   50
 15  \w     38.00  64.00   0.50    1.24    --  111.82 -61.00-120.00   52
 16  \w     88.00 164.00   0.50    1.24    --  111.82  98.00 108.00  152
 17  \w     86.00 158.00   0.50    1.24    --  111.82 111.00  60.00  144
 18  \w     51.00 102.00   0.50    1.24    --  111.82 179.00   0.00  102
 19  \w     42.00 122.00   0.50    1.24    --  111.82 179.00-150.00  160
 20  \w     83.00 144.00   0.50    1.24    --  111.82  61.00  30.00  122
 21  \w    119.00 162.00   0.50    1.24    --  111.82  30.00  60.00   86
 22  \w     79.00 104.00   0.50    1.24    --  111.82  30.00  60.00   50
 23  \w   -132.00-107.00   0.50    0.31    --  -52.00 -94.00  60.00   50
 24  \w   -132.00 -87.00   0.50    0.31    --  -52.00 -94.00  30.00   90
 25  \w   -132.00-107.00   0.50    0.31    --  -52.00 -94.00 -90.00   50
 26  \w   -132.00-107.00   0.50    0.31    --  -52.00 -94.00-120.00   50
 27  \w   -119.00 -94.00   0.50    0.31    --  -52.00 -94.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0339771000
_diffrn_orient_matrix_UB_12      -0.1174907000
_diffrn_orient_matrix_UB_13      -0.0071495000
_diffrn_orient_matrix_UB_21      0.0195067000
_diffrn_orient_matrix_UB_22      -0.1664842000
_diffrn_orient_matrix_UB_23      0.0223103000
_diffrn_orient_matrix_UB_31      -0.0103692000
_diffrn_orient_matrix_UB_32      0.0716622000
_diffrn_orient_matrix_UB_33      0.0401504000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24730
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.088
_diffrn_reflns_theta_min         2.325
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             3904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         9086
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0909
_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/[\s^2^(Fo^2^)+(0.1831P)^2^+7.4147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2569
_refine_ls_wR_factor_ref         0.2806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6483
_reflns_number_total             9086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01503k2.cif
_cod_data_source_block           7050-a-100k_autored
_cod_depositor_comments
'Adding full bibliography for 1574583--1574585.cif.'
_cod_database_code               1574583
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.741
_shelx_estimated_absorpt_t_min   0.691
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O1A-C53A = O1-C53
 1.43 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Br1 \\sim Br2 \\sim Br3 \\sim Br4 \\sim Br5 \\sim Br6 \\sim Br7 \\sim Br8:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O2 \\sim O1 \\sim O4 \\sim O3 \\sim O1A: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
C53 \\sim O1 \\sim C53A \\sim O1A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 Br1, Br2, Br3, Br4, Br5, Br6, Br7, Br8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O2, O1, O4, O3, O1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C53A, O1A, C53, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 1*[Sof(Br1)]+1*[Sof(Br2)]+1*[Sof(Br3)]+1*[Sof(Br4)]+1*[Sof(Br5)]+1*[Sof(Br6)]+
 1*[Sof(Br7)]+1*[Sof(Br8)]=2 with esd of 0
 Sof(O1A)=Sof(H1AA)=Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(9)
 Sof(O1)=Sof(H1A)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=FVAR(9)
6.a Riding coordinates:
 O2(H2A,H2B), O1(H1A), O4(H4A,H4B), O3(H3A,H3B), O1A(H1AA)
6.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C18(H18A,H18B)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C50(H50), C8(H8), C17(H17), C24(H24), C3(H3), C11(H11), C2(H2),
 C10(H10), C5(H5), C37(H37), C34(H34), C14(H14), C36(H36), C35(H35), C16(H16),
 C15(H15), C41(H41), C51(H51), C21(H21), C31(H31), C42(H42), C44(H44), C46(H46),
  C48(H48), C22(H22), C30(H30), C26(H26), C28(H28), C43(H43), C49(H49),
 C23(H23), C29(H29)
6.d Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C53A(H53D,H53E,H53F)
;
_shelx_res_checksum              62376
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.556
_oxdiff_exptl_absorpt_empirical_full_min 0.493