Construction of dibenzo[1,4]oxazocines <i>via</i> palladium-catalysed arylalkylation of allenamides.
Pu, Yue; Xue, Qiaoli; Yan, Liqin; Xie, Xiaotian; Zhao, Haixia; Tang, Kaijie; Shang, Yongjia; Wang, Jian; Chemical communications (Cambridge, England) 61 (2025) 14645–14648; doi:10.1039/d5cc03161c

data_1575457
_publ_section_title
;
 Construction of dibenzo[1,4]oxazocines <i>via</i> palladium-catalysed
 arylalkylation of allenamides.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14645
_journal_page_last               14648
_journal_paper_doi               10.1039/d5cc03161c
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C32 H24 Cl N3 O3 S'
_chemical_formula_sum            'C32 H24 Cl N3 O3 S'
_chemical_formula_weight         566.05
_chemical_name_systematic
(Z)-2-benzyl-2-((9-chloro-5-tosyl-5H-dibenzo[b,g][1,4]oxazocin-7-yl)methyl)malononitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-07-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-19 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                105.538(2)
_cell_angle_beta                 94.907(2)
_cell_angle_gamma                105.754(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1264(4)
_cell_length_b                   12.8330(6)
_cell_length_c                   13.3568(6)
_cell_measurement_reflns_used    8974
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.273
_cell_measurement_theta_min      3.486
_cell_volume                     1429.26(11)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (Bruker, 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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Bruker PHOTON-II area detector'
_diffrn_detector_area_resol_mean 7.4
_diffrn_detector_type            'CMOS-PHOTONII area detector'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON-II area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15249
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.679
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.174
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1414 before and 0.0957 after correction.
The Ratio of minimum to maximum transmission is 0.5289.
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    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.4144
_exptl_crystal_size_mid          0.1631
_exptl_crystal_size_min          0.0799
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0851
_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^)+(0.1654P)^2^+0.3777P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2577
_refine_ls_wR_factor_ref         0.2817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4333
_reflns_number_total             5443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03161c2.cif
_cod_data_source_block           20250718g
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1575457.cif.
;
_cod_database_code               1575457
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.466
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              60212
_shelx_hkl_checksum              42298
_olex2_submission_special_instructions 'No special instructions were received'