Double strain-release enables formal C-O/C-F and C-N/C-F ring-opening metathesis.
Zhu, Yulei; Jia, Jie; Song, Xiangyu; Gong, Chunyu; Xia, Ying; Chemical science 15 (2024) 13800–13806; doi:10.1039/d4sc03624g

data_1572203
_publ_section_title
;
 Double strain-release enables formal C-O/C-F and C-N/C-F ring-opening
 metathesis.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              13800
_journal_page_last               13806
_journal_paper_doi               10.1039/d4sc03624g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C30 H27 F2 N'
_chemical_formula_sum            'C30 H27 F2 N'
_chemical_formula_weight         439.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-11 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.072(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2817(6)
_cell_length_b                   12.1775(11)
_cell_length_c                   24.094(2)
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.38
_cell_volume                     2423.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.0
_diffrn_measured_fraction_theta_full 0.999
_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  0.0724
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30065
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.381
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0953 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9293.
The \l/2 correction factor is Not present.
;
_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    1.204
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0122(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5558
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0581P)^2^+0.6569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2837
_reflns_number_total             5558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03624g2.cif
_cod_data_source_block           mo_xy_jj_1_0ma_a
_cod_depositor_comments          'Adding full bibliography for 1572203.cif.'
_cod_original_cell_volume        2423.8(4)
_cod_database_code               1572203
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C27, F28
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C27 \\sim F28: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
4.a Ternary CH refined with riding coordinates:
 C5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C25(H25A,H25B), C27(H27A,H27B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C28(H28), C3(H3), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C29(H29), C30(H30)
4.d X=CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_shelx_res_checksum              7658
_shelx_hkl_checksum              80996
_olex2_submission_special_instructions 'No special instructions were received'