A simple method to modulate the selectivity of aryl azide photolysis using cucurbit[8]uril.
Qiu, Xujun; Cai, Qianyu; Pohl, Eric; Jung, André; Su, Haopu; Fuhr, Olaf; Schepers, Ute; Bräse, Stefan; Chemical communications (Cambridge, England) 60 (2024) 12852–12855; doi:10.1039/d4cc04209c

data_7133806
_publ_section_title
;
 A simple method to modulate the selectivity of aryl azide photolysis
 using cucurbit[8]uril.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12852
_journal_page_last               12855
_journal_paper_doi               10.1039/d4cc04209c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'Cl, H2 O, C26 H23 N2, 0.5(C2 H3 N)'
_chemical_formula_sum            'C27 H26.5 Cl N2.5 O'
_chemical_formula_weight         437.46
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-12 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.802(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.0721(3)
_cell_length_b                   19.0557(5)
_cell_length_c                   23.2446(8)
_cell_measurement_reflns_used    29415
_cell_measurement_temperature    180
_cell_measurement_theta_max      63.92
_cell_measurement_theta_min      3.32
_cell_volume                     4445.7(2)
_computing_cell_refinement
;
X-Area Recipe 2.0.1 (STOE, 2023)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.192.0 (STOE, 2023)
;
_computing_data_reduction
;
X-Area Integrate 2.5.15.0 (STOE, 2023)
X-Area LANA 2.7.12 (STOE, 2023)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.3, Darmstadt 2023
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      180
_diffrn_detector                 'Eiger R 4M'
_diffrn_detector_area_resol_mean 13.33
_diffrn_detector_type            DECTRIS
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
 1419 frames, detector distance = 80 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            54227
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.597
_diffrn_reflns_theta_max         62.499
_diffrn_reflns_theta_min         3.320
_diffrn_source                   'Metal Jet D2+'
_diffrn_source_current           3.57
_diffrn_source_power             0.250
_diffrn_source_target            Ga
_diffrn_source_type              'Metal Jet D2+'
_diffrn_source_voltage           70
_exptl_absorpt_coefficient_mu    1.114
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_correction_T_min  0.8763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.918
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         10646
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0587
_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^)+(0.1174P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1777
_refine_ls_wR_factor_ref         0.1883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7147
_reflns_number_total             10646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04209c2.cif
_cod_data_source_block           xqr320suvb
_cod_depositor_comments
'Adding full bibliography for 7133804--7133806.cif.'
_cod_original_formula_sum        'C27 H26.50 Cl N2.50 O'
_cod_database_code               7133806
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.878
_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,H) groups
2. Restrained distances
 C53B-C54B
 1.54 with sigma of 0.02
 C53B-N5B
 1.2 with sigma of 0.02
3. Others
 Fixed Sof: N5A(0.75) C53A(0.75) C54A(0.75) H54A(0.75) H54B(0.75) H54C(0.75)
 N5B(0.25) C53B(0.25) C54B(0.25) H54D(0.25) H54E(0.25) H54F(0.25)
4.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B), C16(H16A,H16B), C33(H33A,H33B),
 C34(H34A,H34B), C41(H41A,H41B), C42(H42A,H42B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C21(H21), C22(H22), C23(H23), C24(H24), N3(H3), C30(H30), C31(H31), C36(H36),
 C37(H37), C39(H39), C40(H40), C43(H43), C47(H47), C48(H48), C49(H49), C50(H50)
4.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C52(H52A,H52B,H52C), C54A(H54A,H54B,H54C), C54B(H54D,
 H54E,H54F)
;
_shelx_res_checksum              39268
_shelx_hkl_checksum              78321
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '80.0 mm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_size_x            '15.5 cm'
_stoe_detector_size_y            '16.2 cm'
_stoe_evaluation_integration_a   18.0
_stoe_evaluation_integration_b   0.4
_stoe_evaluation_integration_ems 0.014
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 98.7
_stoe_evaluation_lana_dxs_max_order -
_stoe_evaluation_lana_dys_max_order -
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 128.3
_stoe_evaluation_lana_max_2theta_desired 125.0
_stoe_evaluation_lana_mean_redundancy 5.1
_stoe_evaluation_lana_number_refls_after_or 54227
_stoe_evaluation_lana_number_refls_outliers 3304
_stoe_evaluation_lana_number_refls_total 57531
_stoe_evaluation_lana_number_refls_unique 10646
_stoe_evaluation_lana_number_refls_written 54227
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group 2/m
_stoe_evaluation_lana_table
;
2Theta          12.2   25.6   39.0   52.4   65.8   79.2   92.6  106.0  119.4
<Resolution>    5.38   2.84   1.93   1.50   1.23   1.06   0.93   0.84   0.78
N(total)         117    695   2569   8277  10280  10167  10991   9025   5410
<Redundancy>     1.8    2.4    3.9    7.7    7.2    5.7    5.5    4.3    3.0
Complet. [%%]    92.4   97.0   99.8  100.0  100.0   98.4   99.8   99.7   95.4
<I/sigma>      207.7  111.3   40.8   19.4   10.6    7.1    3.5    2.5    1.9
R(int)         0.012  0.010  0.016  0.022  0.033  0.045  0.085  0.108  0.133
;
_stoe_measurement_identifier     XQR320SUVB
_stoe_measurement_max_exposure_per_frame '1.0 s'
_stoe_measurement_mean_exposure_per_frame '1.0 s'
_stoe_measurement_min_exposure_per_frame '1.0 s'
_stoe_measurement_total_exposure_time '24 min'
_stoe_measurement_total_frame_number 1419
_stoe_measurement_total_run_number 17
_stoe_measurement_tube_power     '250 W'