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_7249661
_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_absolute_configuration rmad
_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 96.7100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.84010(10)
_cell_length_b                   12.40940(10)
_cell_length_c                   12.46850(10)
_cell_measurement_reflns_used    15612
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.5310
_cell_measurement_theta_min      3.5160
_cell_volume                     1204.76(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.118a 64-bit (release 27-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (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_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_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     23.00 120.00   0.50    0.06    --   46.74  77.00 120.00  194
  2  \w     23.00 120.00   0.50    0.06    --   46.74  77.00   0.00  194
  3  \w     31.00 120.00   0.50    0.06    --   46.74  57.00 -30.00  178
  4  \w     31.00 120.00   0.50    0.06    --   46.74  57.00  90.00  178
  5  \w     23.00 120.00   0.50    0.06    --   46.74  77.00-120.00  194
  6  \w     31.00 120.00   0.50    0.06    --   46.74  57.00-150.00  178
  7  \w     99.00 176.00   0.50    0.25    --  113.25  45.00 -90.00  154
  8  \w     99.00 176.00   0.50    0.25    --  113.25  45.00 -60.00  154
  9  \w     99.00 176.00   0.50    0.25    --  113.25  30.00-150.00  154
 10  \w     99.00 176.00   0.50    0.25    --  113.25  30.00-150.00  154
 11  \w     96.00 176.00   0.50    0.25    --  113.25  15.00-120.00  160
 12  \w     41.00 106.00   0.50    0.25    --  113.25 -95.00-180.00  130
 13  \w     41.00 106.00   0.50    0.25    --  113.25 -95.00 -90.00  130
 14  \w     43.00 111.00   0.50    0.25    --  113.25-125.00 -90.00  136
 15  \w     41.00 106.00   0.50    0.25    --  113.25 -95.00 -30.00  130
 16  \w     41.00 106.00   0.50    0.25    --  113.25 -95.00  90.00  130
 17  \w     41.00 105.00   0.50    0.25    --  113.25 -77.00 150.00  128
 18  \w     41.00 105.00   0.50    0.25    --  113.25 -77.00 150.00  128
 19  \w    -27.00  43.00   0.50    0.06    --   46.74 -38.00 120.00  140
 20  \w    -29.00  26.00   0.50    0.06    --   46.74 -19.00  30.00  110
 21  \w     41.00  71.00   0.50    0.25    --  113.25 -61.00-180.00   60
 22  \w    -27.00  43.00   0.50    0.06    --   46.74 -38.00-120.00  140
 23  \w   -119.00 -23.00   0.50    0.06    --  -46.74 -77.00 -90.00  192
 24  \w   -119.00 -46.00   0.50    0.06    --  -46.74 -77.00  30.00  146
 25  \w   -175.00 -87.00   0.50    0.25    -- -105.00 -15.00   0.00  176
 26  \w   -175.00 -81.00   0.50    0.25    -- -105.00 -77.00  30.00  188
 27  \w   -175.00 -90.00   0.50    0.25    -- -105.00 -52.00 104.48  170
 28  \w   -122.00 -31.00   0.50    0.06    --  -46.74 -19.00 120.00  182
 29  \w    -43.00  27.00   0.50    0.06    --  -46.74  38.00 120.00  140
 30  \w    -71.00 -32.00   0.50    0.25    -- -105.00  61.00 150.00   78
 31  \w   -105.00 -32.00   0.50    0.25    -- -105.00  77.00  60.00  146
 32  \w    -71.00 -32.00   0.50    0.25    -- -105.00  61.00  30.00   78
 33  \w    -71.00 -32.00   0.50    0.25    -- -105.00  61.00   0.00   78
 34  \w    -71.00 -32.00   0.50    0.25    -- -105.00  61.00 -90.00   78
 35  \w   -108.00 -35.00   0.50    0.25    -- -105.00 109.00  51.89  146
 36  \w   -112.00 -35.00   0.50    0.25    -- -105.00 125.00 -30.00  154
 37  \w   -132.00 -32.00   0.50    0.25    -- -105.00 155.00  74.82  200
 38  \w   -112.00 -35.00   0.50    0.25    -- -105.00 125.00  60.00  154
 39  \w   -127.00 -32.00   0.50    0.25    -- -105.00 146.00-131.97  190
 40  \w   -127.00 -32.00   0.50    0.25    -- -105.00 146.00-131.97  190
 41  \w    -93.00 -13.00   0.50    0.06    --  -46.74 125.00-150.00  160
 42  \w    113.00 138.00   0.50    0.25    --  113.25  19.00 137.00   50
 43  \w   -120.00 -24.00   0.50    0.06    --  -47.73 -77.00 120.00  192
 44  \w    -26.00  28.00   0.50    0.06    --  -47.73  19.00  30.00  108
 45  \w   -120.00 -24.00   0.50    0.06    --  -47.73 -77.00   0.00  192
 46  \w   -120.00 -31.00   0.50    0.06    --  -47.73 -57.00-180.00  178
 47  \w   -121.00 -33.00   0.50    0.06    --  -47.73 -38.00  90.00  176
 48  \w   -120.00 -24.00   0.50    0.06    --  -47.73 -77.00 -60.00  192
 49  \w   -121.00 -33.00   0.50    0.06    --  -47.73 -38.00 -60.00  176
 50  \w   -121.00 -33.00   0.50    0.06    --  -47.73 -38.00   0.00  176
 51  \w     24.00 120.00   0.50    0.06    --   47.73  77.00  90.00  192
 52  \w    -26.00  43.00   0.50    0.06    --   47.73 -38.00   0.00  138
 53  \w     24.00 120.00   0.50    0.06    --   47.73  77.00-180.00  192
 54  \w   -175.00-128.00   0.50    0.25    -- -105.00 -46.00 154.98   94
 55  \w   -175.00 -90.00   0.50    0.25    -- -105.00 -45.00  60.00  170
 56  \w     96.00 176.00   0.50    0.25    --  113.25  15.00-180.00  160
;
_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      0.1790660000
_diffrn_orient_matrix_UB_12      -0.0189314000
_diffrn_orient_matrix_UB_13      -0.0359188000
_diffrn_orient_matrix_UB_21      -0.0834675000
_diffrn_orient_matrix_UB_22      -0.0252269000
_diffrn_orient_matrix_UB_23      -0.1153101000
_diffrn_orient_matrix_UB_31      0.0106951000
_diffrn_orient_matrix_UB_32      0.1200589000
_diffrn_orient_matrix_UB_33      -0.0298925000
_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  0.0576
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32451
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.841
_diffrn_reflns_theta_min         3.569
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0659P)^2^+0.0770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.823
_reflns_Friedel_fraction_max     0.763
_reflns_number_gt                4215
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01123f2.cif
_cod_data_source_block           b
_cod_depositor_comments
'Adding full bibliography for 7249659--7249661.cif.'
_cod_database_code               7249661
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.776
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), N5(H5), N2(H2), C11(H11), C12(H12), C10(H10), C8(H8),
 C20(H20), C9(H9), C16(H16), C19(H19), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 N8(H8A,H8B,H8C), N7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              4108
_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.648