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

data_7155882
_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         'C25 H22 O5'
_chemical_formula_sum            'C25 H22 O5'
_chemical_formula_weight         402.42
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-09-08 deposited with the CCDC.
2017-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.2910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5283(2)
_cell_length_b                   14.2319(3)
_cell_length_c                   14.0529(3)
_cell_measurement_reflns_used    9304
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.3204
_cell_measurement_theta_min      2.4639
_cell_volume                     2031.11(7)
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      172.98
_diffrn.ambient_temp_esd         2.0
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker Photon 50'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  BrukerD8QuestEco
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker Photon 50'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24893
_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         26.377
_diffrn_reflns_theta_min         2.805
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens KFFMO2K--90C'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0513P)^2^+0.6734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2954
_reflns_number_total             4141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01697b2.cif
_cod_data_source_block           dt1735_0m_a
_cod_database_code               7155882
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.981
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H00C)=Sof(H00D)=Sof(H00O)=Sof(H00P)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=
 Sof(O00V)=1-FVAR(1)
 Sof(H00A)=Sof(H00B)=Sof(H00E)=Sof(H00J)=Sof(C00T)=Sof(H00Y)=Sof(H)=Sof(O00U)=
 FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C00J(H00C,H00D), C00J(H00A,H00B), C00O(H00E,H00J), C00O(H00O,H00P), C00T(H00Y,
 H), C0AA(H0AA,H0AB)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00Q), C00Q(H00R)
3.c Idealised Me refined as rotating group:
 C00R(H00S,H00T,H00U), C00S(H00V,H00W,H00X)
;
_olex2_submission_special_instructions 'No special instructions were received'