A photoluminescent second-order nonlinear optical molecular crystal with cold crystallization
Shen, Xin; Qi, Jun-Chao; Peng, Hang; Xia, Zhang-Tian; Bai, Yong-Ju; Chen, Hui-Ping; Wang, Zhen-Yu; Yang, Tian-En; Qin, Yan; Liao, Wei-Qiang; CrystEngComm 27 (2025) 1381–1385; doi:10.1039/D4CE01322K

data_7249987
_publ_section_title
;
 A photoluminescent second-order nonlinear optical molecular crystal with
 cold crystallization
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1381
_journal_page_last               1385
_journal_paper_doi               10.1039/D4CE01322K
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 Br2 N2 O2'
_chemical_formula_sum            'C20 H20 Br2 N2 O2'
_chemical_formula_weight         480.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-09-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-07 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9191(3)
_cell_length_b                   19.0670(7)
_cell_length_c                   9.0123(5)
_cell_measurement_reflns_used    2369
_cell_measurement_temperature    298.01(10)
_cell_measurement_theta_max      71.6240
_cell_measurement_theta_min      4.6250
_cell_volume                     1017.12(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_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_environment      air
_diffrn_ambient_temperature      298.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.929
_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     58.00  92.00   0.50    0.05    --   75.18 167.00  95.00   68
  2  \w     69.00 110.00   0.50    0.05    --   60.54  30.00 -90.00   82
  3  \w     11.00  38.00   0.50    0.05    --   60.54 -30.00   0.00   54
  4  \w     11.00  37.00   0.50    0.05    --   60.54 -30.00 -90.00   52
  5  \w     11.00  36.00   0.50    0.05    --   60.54 -30.00-180.00   50
  6  \w     37.00  80.00   0.50    0.05    --   75.18 -94.00-120.00   86
  7  \w     66.00  91.00   0.50    0.05    --   60.54-167.00  75.00   50
  8  \w     34.00  78.00   0.50    0.05    --   75.18-115.00-138.00   88
  9  \w     47.00  73.00   0.50    0.05    --   60.54-115.00-138.00   52
 10  \w   -117.00 -75.00   0.50    0.05    --  -75.50-125.00  90.00   84
 11  \w   -114.00 -89.00   0.50    0.05    --  -74.13-125.00 150.00   50
 12  \w    -87.00 -61.00   0.50    0.05    --  -74.13-167.00  75.00   52
 13  \w   -118.00 -79.00   0.50    0.05    --  -74.13-125.00  30.00   78
 14  \w   -108.00 -82.00   0.50    0.05    --  -74.13-125.00 -60.00   52
 15  \w   -101.00 -73.00   0.50    0.05    --  -74.13-125.00-150.00   56
 16  \w   -106.00 -81.00   0.50    0.05    --  -74.13 -30.00  90.00   50
 17  \w   -119.00 -94.00   0.50    0.05    --  -74.13 -30.00  30.00   50
 18  \w    -51.00 -26.00   0.50    0.05    --  -60.72 115.00 -49.00   50
 19  \w    -84.00 -38.00   0.50    0.05    --  -60.72 167.00  95.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196786000
_diffrn_orient_matrix_UB_12      0.0710847000
_diffrn_orient_matrix_UB_13      0.0801410000
_diffrn_orient_matrix_UB_21      0.2559404000
_diffrn_orient_matrix_UB_22      -0.0115454000
_diffrn_orient_matrix_UB_23      0.0186033000
_diffrn_orient_matrix_UB_31      0.0424617000
_diffrn_orient_matrix_UB_32      0.0366691000
_diffrn_orient_matrix_UB_33      -0.1498627000
_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  0.0774
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4211
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.937
_diffrn_reflns_theta_min         4.638
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.681
_refine_diff_density_min         -1.020
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Flack x determined using 349 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0730
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1621
_reflns_Friedel_coverage         0.545
_reflns_Friedel_fraction_full    0.810
_reflns_Friedel_fraction_max     0.752
_reflns_number_gt                1272
_reflns_number_total             1721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01322k2.cif
_cod_data_source_block           SS-C20H20Br2N2O2-298K
_cod_depositor_comments
'Adding full bibliography for 7249987--7249989.cif.'
_cod_database_code               7249987
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N F'
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4), C2(H2)
2.d Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              67252
_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 8.653
_oxdiff_exptl_absorpt_empirical_full_min 0.107