Chiral-driven formation of hybrid cyanurates with large birefringence
Zhao, Yue; Hu, Chun-Li; Chen, Peng-Fei; Zhang, Ming-Zhi; Mao, Jiang-Gao; CrystEngComm 27 (2025) 30–37; doi:10.1039/D4CE01123F

data_7249659
_publ_section_title
;
 Chiral-driven formation of hybrid cyanurates with large birefringence
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              30
_journal_page_last               37
_journal_paper_doi               10.1039/D4CE01123F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C3 H2 N3 O3, C8 H12 N'
_chemical_formula_sum            'C11 H14 N4 O3'
_chemical_formula_weight         250.26
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-05-29 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.410(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9636(3)
_cell_length_b                   6.64630(10)
_cell_length_c                   11.5269(2)
_cell_measurement_reflns_used    4463
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3790
_cell_measurement_theta_min      5.5850
_cell_volume                     1209.84(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_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     55.00  81.00   0.50    0.84    --  108.57 -95.00  90.00   52
  2  \w    -36.00  -9.00   0.50    0.21    --  -46.49  41.00 132.00   54
  3  \w   -100.00 -65.00   0.50    0.84    -- -105.44 125.00 150.00   70
  4  \w   -101.00 -46.00   0.50    0.84    -- -105.44  77.00-180.00  110
  5  \w   -101.00 -75.00   0.50    0.21    --  -46.49 -41.00 -20.00   52
  6  \w   -158.00-133.00   0.50    0.84    -- -105.44 -41.00 -20.00   50
  7  \w    -62.00 -32.00   0.50    0.21    --  -46.49 -41.00 -20.00   60
  8  \w     20.00  46.00   0.50    0.21    --   49.62 -41.00 -20.00   52
  9  \w    -23.00  15.00   0.50    0.21    --   49.62 -41.00 -20.00   76
 10  \w     -9.00  16.00   0.50    0.21    --   49.62 -19.00-150.00   50
 11  \w    -26.00  25.00   0.50    0.21    --   49.62 -19.00-180.00  102
 12  \w     38.00  65.00   0.50    0.84    --  108.57 -61.00 -60.00   54
 13  \w     39.00  64.00   0.50    0.84    --  108.57 -61.00-120.00   50
 14  \w     36.00  71.00   0.50    0.84    --  108.57 -61.00-180.00   70
 15  \w     36.00  71.00   0.50    0.84    --  108.57 -61.00 -30.00   70
 16  \w     43.00  68.00   0.50    0.84    --  108.57 -61.00  30.00   50
 17  \w     36.00  68.00   0.50    0.84    --  108.57 -61.00  60.00   64
 18  \w     37.00  70.00   0.50    0.84    --  108.57 -61.00 120.00   66
 19  \w     36.00  69.00   0.50    0.84    --  108.57 -61.00 150.00   66
 20  \w     38.00  70.00   0.50    0.84    --  108.57 -61.00   0.00   64
 21  \w     38.00  71.00   0.50    0.84    --  108.57 -61.00-150.00   66
 22  \w    125.00 163.00   0.50    0.84    --  108.57  30.00-150.00   76
 23  \w    132.00 172.00   0.50    0.84    --  108.57  45.00  30.00   80
 24  \w     94.00 170.00   0.50    0.84    --  108.57  41.00 132.00  152
 25  \w     39.00 123.00   0.50    0.21    --   49.62  41.00 132.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0882886000
_diffrn_orient_matrix_UB_12      -0.0661972000
_diffrn_orient_matrix_UB_13      -0.0239741000
_diffrn_orient_matrix_UB_21      -0.0403352000
_diffrn_orient_matrix_UB_22      -0.0981584000
_diffrn_orient_matrix_UB_23      -0.1159178000
_diffrn_orient_matrix_UB_31      0.0095542000
_diffrn_orient_matrix_UB_32      0.1992437000
_diffrn_orient_matrix_UB_33      -0.0652362000
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7100
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.895
_diffrn_reflns_theta_min         2.798
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0588P)^2^+0.1886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2085
_reflns_number_total             2429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01123f2.cif
_cod_data_source_block           b-rac
_cod_depositor_comments
'Adding full bibliography for 7249659--7249661.cif.'
_cod_database_code               7249659
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C10(H10)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C9(H9), C5(H5), C8(H8), C6(H6), C7(H7)
4.c Idealised Me refined as rotating group:
 N4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              34056
_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 1.195
_oxdiff_exptl_absorpt_empirical_full_min 0.813