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_7249660
_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 ad
_chemical_formula_moiety         'C3 H2 N3 O3, C8 H12 N'
_chemical_formula_sum            'C11 H14 N4 O3'
_chemical_formula_weight         250.26
_chemical_name_systematic        S-a-MBACY
_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                 96.7460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.84020(10)
_cell_length_b                   12.41110(10)
_cell_length_c                   12.47300(10)
_cell_measurement_reflns_used    30204
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2160
_cell_measurement_theta_min      3.5360
_cell_volume                     1205.29(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -94.00 -13.00   0.50    0.05    --  -47.74 125.00 150.00  162
  2  \w   -108.00 -48.00   0.50    0.45    -- -105.00 125.00 -30.00  120
  3  \w    -73.00 -37.00   0.50    0.45    -- -105.00 125.00 -90.00   72
  4  \w   -111.00 -83.00   0.50    0.45    -- -105.00 125.00 -90.00   56
  5  \w    -25.00  27.00   0.50    0.05    --  -47.74   9.00 -33.00  104
  6  \w     24.00 121.00   0.50    0.05    --   47.74  77.00-120.00  194
  7  \w     32.00 121.00   0.50    0.05    --   47.74  57.00 -90.00  178
  8  \w     20.00 123.00   0.50    0.05    --   47.74   9.00 -33.00  206
  9  \w     32.00 121.00   0.50    0.05    --   47.74  57.00   0.00  178
 10  \w     32.00 121.00   0.50    0.05    --   47.74  57.00  60.00  178
 11  \w     85.00 173.00   0.50    0.45    --  108.08  77.00 -30.00  176
 12  \w     80.00 176.00   0.50    0.45    --  108.08   9.00 -33.00  192
 13  \w    -26.00  43.00   0.50    0.05    --   47.74 -38.00   0.00  138
 14  \w    -27.00  25.00   0.50    0.05    --   47.74  -9.00 152.00  104
 15  \w     36.00 104.00   0.50    0.45    --  108.08 -77.00  30.00  136
 16  \w     69.00 103.00   0.50    0.45    --  108.08 -77.00 120.00   68
 17  \w     41.00  66.00   0.50    0.45    --  108.08 -77.00 120.00   50
 18  \w     37.00  95.00   0.50    0.45    --  108.08 -77.00  90.00  116
 19  \w     60.00 101.00   0.50    0.45    --  108.08 -95.00 120.00   82
 20  \w     39.00  64.00   0.50    0.45    --  108.08-125.00  90.00   50
 21  \w     73.00 111.00   0.50    0.45    --  108.08-125.00  90.00   76
 22  \w     13.00  94.00   0.50    0.05    --   47.74-125.00  60.00  162
 23  \w     39.00  64.00   0.50    0.45    --  108.08-125.00 -30.00   50
 24  \w     36.00  93.00   0.50    0.45    --  108.08 -95.00   0.00  114
 25  \w     77.00 112.00   0.50    0.45    --  108.08-125.00 -30.00   70
 26  \w     35.00 105.00   0.50    0.45    --  108.08 -95.00 -90.00  140
 27  \w     63.00 112.00   0.50    0.45    --  108.08-125.00-120.00   98
 28  \w     39.00  93.00   0.50    0.45    --  108.08-125.00 -90.00  108
 29  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00  90.00  192
 30  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 120.00  192
 31  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 150.00  192
 32  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00  90.00  192
 33  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00  30.00  192
 34  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 -30.00  192
 35  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00 -60.00  192
 36  \w   -120.00 -31.00   0.50    0.05    --  -47.74 -57.00 -90.00  178
 37  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00-120.00  192
 38  \w   -120.00 -24.00   0.50    0.05    --  -47.74 -77.00-180.00  192
 39  \w   -121.00 -33.00   0.50    0.05    --  -47.74 -38.00 -90.00  176
 40  \w   -121.00 -33.00   0.50    0.05    --  -47.74 -38.00 -90.00  176
 41  \w   -120.00 -32.00   0.50    0.05    --  -47.74 -46.00 110.08  176
 42  \w   -121.00 -33.00   0.50    0.05    --  -47.74 -38.00 120.00  176
 43  \w   -123.00 -23.00   0.50    0.05    --  -47.74  -9.00 152.00  200
 44  \w   -123.00 -23.00   0.50    0.05    --  -47.74  -9.00 152.00  200
 45  \w   -175.00-137.00   0.50    0.45    -- -105.00 -77.00  53.55   76
 46  \w   -169.00-143.00   0.50    0.45    -- -105.00 -77.00 150.00   52
 47  \w   -107.00 -81.00   0.50    0.45    -- -105.00 -77.00  53.55   52
 48  \w   -109.00 -81.00   0.50    0.45    -- -105.00 -77.00 150.00   56
 49  \w   -110.00 -81.00   0.50    0.45    -- -105.00 -77.00   0.00   58
 50  \w   -109.00 -82.00   0.50    0.45    -- -105.00 -77.00 -30.00   54
 51  \w   -174.00 -81.00   0.50    0.45    -- -105.00 -76.00 -51.49  186
 52  \w   -172.00-146.00   0.50    0.45    -- -105.00 -77.00   0.00   52
 53  \w   -109.00 -82.00   0.50    0.45    -- -105.00 -75.00  10.57   54
 54  \w   -108.00 -82.00   0.50    0.45    -- -105.00 -75.00 -38.00   52
 55  \w   -108.00 -82.00   0.50    0.45    -- -105.00 -75.00 -44.53   52
 56  \w   -113.00 -86.00   0.50    0.45    -- -105.00 -77.00-150.00   54
 57  \w   -175.00-116.00   0.50    0.45    -- -105.00 -77.00-150.00  118
 58  \w   -145.00-120.00   0.50    0.45    -- -105.00 -75.00 -38.00   50
 59  \w   -173.00-121.00   0.50    0.45    -- -105.00 -75.00  10.57  104
 60  \w   -164.00-137.00   0.50    0.45    -- -105.00 -71.00 -64.94   54
 61  \w   -117.00 -84.00   0.50    0.45    -- -105.00 -71.00 -64.94   66
 62  \w   -111.00 -85.00   0.50    0.45    -- -105.00 -68.00 112.31   52
 63  \w   -109.00 -83.00   0.50    0.45    -- -105.00 -72.00 151.01   52
 64  \w   -118.00 -85.00   0.50    0.45    -- -105.00 -67.00 124.74   66
 65  \w   -109.00 -83.00   0.50    0.45    -- -105.00 -72.00 175.53   52
 66  \w   -111.00 -85.00   0.50    0.45    -- -105.00 -68.00 177.49   52
 67  \w   -170.00 -86.00   0.50    0.45    -- -105.00 -64.00 152.40  168
 68  \w   -168.00-119.00   0.50    0.45    -- -105.00 -72.00 175.53   98
 69  \w   -173.00-148.00   0.50    0.45    -- -105.00 -68.00 112.31   50
 70  \w   -170.00 -86.00   0.50    0.45    -- -105.00 -64.00 115.66  168
 71  \w   -122.00 -86.00   0.50    0.45    -- -105.00 -64.00 100.06   72
 72  \w   -124.00 -86.00   0.50    0.45    -- -105.00 -64.00  16.76   76
 73  \w   -171.00-145.00   0.50    0.45    -- -105.00 -64.00  16.76   52
 74  \w   -170.00-145.00   0.50    0.45    -- -105.00 -63.00 -83.03   50
 75  \w   -121.00 -87.00   0.50    0.45    -- -105.00 -63.00 -91.37   68
 76  \w   -113.00 -88.00   0.50    0.45    -- -105.00 -63.00 -83.03   50
 77  \w   -170.00 -87.00   0.50    0.45    -- -105.00 -63.00-140.64  166
 78  \w   -163.00 -86.00   0.50    0.45    -- -105.00 -65.00-130.33  154
 79  \w   -125.00 -87.00   0.50    0.45    -- -105.00 -61.00   0.00   76
 80  \w   -172.00 -87.00   0.50    0.45    -- -105.00 -61.00 -30.00  170
 81  \w   -120.00 -88.00   0.50    0.45    -- -105.00 -62.00  86.87   64
 82  \w   -112.00 -87.00   0.50    0.45    -- -105.00 -61.00  90.00   50
 83  \w   -152.00 -87.00   0.50    0.45    -- -105.00 -62.00  77.23  130
 84  \w   -175.00-134.00   0.50    0.45    -- -105.00 -61.00  90.00   82
 85  \w   -128.00 -90.00   0.50    0.45    -- -105.00 -61.00-120.00   76
 86  \w   -131.00 -89.00   0.50    0.45    -- -105.00 -60.00-128.17   84
 87  \w   -113.00 -88.00   0.50    0.45    -- -105.00 -59.00-115.62   50
 88  \w   -118.00 -89.00   0.50    0.45    -- -105.00 -55.00-161.40   58
 89  \w   -152.00-126.00   0.50    0.45    -- -105.00 -59.00-115.62   52
 90  \w   -170.00 -89.00   0.50    0.45    -- -105.00 -56.00-110.85  162
 91  \w   -117.00 -88.00   0.50    0.45    -- -105.00 -59.00  21.37   58
 92  \w   -128.00 -88.00   0.50    0.45    -- -105.00 -54.00  34.23   80
 93  \w   -116.00 -88.00   0.50    0.45    -- -105.00 -54.00  56.39   56
 94  \w   -124.00 -88.00   0.50    0.45    -- -105.00 -54.00  45.02   72
 95  \w   -174.00 -90.00   0.50    0.45    -- -105.00 -54.00 134.99  168
 96  \w   -171.00-142.00   0.50    0.45    -- -105.00 -45.00 174.23   58
 97  \w   -121.00 -90.00   0.50    0.45    -- -105.00 -45.00 174.23   62
 98  \w   -126.00 -90.00   0.50    0.45    -- -105.00 -44.00 164.31   72
 99  \w   -175.00 -81.00   0.50    0.45    -- -105.00  -9.00 152.00  188
100  \w   -165.00-139.00   0.50    0.45    -- -105.00 -54.00  56.39   52
101  \w   -115.00 -89.00   0.50    0.45    -- -105.00 -51.00 -57.00   52
102  \w   -126.00 -90.00   0.50    0.45    -- -105.00 -45.00 -60.00   72
;
_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      0.1020791000
_diffrn_orient_matrix_UB_12      -0.0079272000
_diffrn_orient_matrix_UB_13      0.1130498000
_diffrn_orient_matrix_UB_21      -0.1691094000
_diffrn_orient_matrix_UB_22      -0.0135707000
_diffrn_orient_matrix_UB_23      0.0502428000
_diffrn_orient_matrix_UB_31      0.0120622000
_diffrn_orient_matrix_UB_32      -0.1230998000
_diffrn_orient_matrix_UB_33      -0.0128655000
_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  0.0407
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44159
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.526
_diffrn_reflns_theta_min         3.568
_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  0.54070
_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            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0610P)^2^+0.0813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                4596
_reflns_number_total             4730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01123f2.cif
_cod_data_source_block           c-s
_cod_depositor_comments
'Adding full bibliography for 7249659--7249661.cif.'
_cod_database_code               7249660
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H14 N4 O3'
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.608
_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:
 N5(H5), N2(H2), N1(H1), N4(H4), C12(H12), C10(H10), C9(H9), C8(H8), C16(H16),
 C11(H11), C20(H20), C17(H17), C19(H19), 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              69584
_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 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.558