Photochemical Generation and Trapping of 3-Oxacyclohexyne
Fan, Rui; Wen, Yuewei; Thamattoor, Dasan Madhav; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01697B

data_7155881
_publ_section_title
;
 Photochemical Generation and Trapping of 3-Oxacyclohexyne
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01697B
_journal_year                    2017
_chemical_formula_moiety         'C19 H16 O'
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.32
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-06 deposited with the CCDC.
2017-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.46
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.482
_cell_length_b                   5.173
_cell_length_c                   12.755
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.72
_cell_volume                     684.094
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8730
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.858
_diffrn_reflns_theta_min         2.720
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0567 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.9387. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_preparation       'Takeda Reaction'
_exptl_crystal_recrystallization_method 'Hexanes/EtOAc (column fraction)'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.875
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2155
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01697b2.cif
_cod_data_source_block           dt1716a_0m_a
_cod_original_cell_volume        684.1
_cod_database_code               7155881
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Sof(H19C)=Sof(H19D)=Sof(H17A)=Sof(H17B)=Sof(O1A)=Sof(C18A)=Sof(H18A)=
 Sof(H18B)=1-FVAR(1)
 Sof(O1)=Sof(H15A)=Sof(H15B)=Sof(H19A)=Sof(H19B)=Sof(C18)=Sof(H20A)=Sof(H20B)=
 FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C14(H14), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C19(H15A,H15B), C19(H19C,H19D), C17(H19A,H19B), C17(H17A,H17B), C18(H20A,
 H20B), C18A(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C12(H12), C9(H9), C3(H3), C11(H11), C5(H5), C4(H4)
;
_shelx_res_checksum              34534
_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id DT1716a
_olex2_submission_special_instructions 'No special instructions were received'