Isomer-dependent reactivity in the solid state: topochemical [4 + 4] <i>vs.</i> [4 + 2] cycloaddition reactions.
Lal, Anu; Sureshan, Kana M.; Chemical science 16 (2025) 13496–13502; doi:10.1039/d5sc02327k

data_1574887
_publ_section_title
;
 Isomer-dependent reactivity in the solid state: topochemical [4 + 4]
 <i>vs.</i> [4 + 2] cycloaddition reactions.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              13496
_journal_page_last               13502
_journal_paper_doi               10.1039/d5sc02327k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C21 H13 N3 O2'
_chemical_formula_sum            'C21 H13 N3 O2'
_chemical_formula_weight         339.34
_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     iterative
_audit_creation_date             2024-04-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-07 deposited with the CCDC.	2025-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.189(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8447(2)
_cell_length_b                   12.8869(8)
_cell_length_c                   30.8271(16)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      3.16
_cell_volume                     1526.25(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      110.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            36877
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         2.536
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1149 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.9587.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0622P)^2^+0.4328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3242
_reflns_number_total             3762
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02327k2.cif
_cod_data_source_block           anths1r_a
_cod_depositor_comments
'Adding full bibliography for 1574887--1574888.cif.'
_cod_database_code               1574887
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.995
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C10(H10), C20(H20), C19(H19), C1(H1), C5(H5), C4(H4),
 C2(H2), C7(H7), C8(H8), C3(H3), C6(H6)
;
_shelx_res_checksum              54492
_olex2_submission_special_instructions 'No special instructions were received'