Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products
Haughey, Maxwell B.; Christensen, Kirsten E.; Poole, Darren L.; Donohoe, Timothy J.; Chemical Science  (2021) –; doi:10.1039/D1SC04247E

data_1564697
_publ_section_title
;
 Development of an enolate alkynylation approach towards the synthesis of
 the taiwanschirin natural products
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04247E
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H16 O5'
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.29
_chemical_melting_point          ?
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-08-16
_audit_creation_method           CRYSTALS_ver_14.61_build_6720
_audit_update_record
;
2021-03-23 deposited with the CCDC.	2021-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0413(3)
_cell_length_b                   7.0334(2)
_cell_length_c                   27.4163(9)
_cell_measurement_reflns_used    5831
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      6
_cell_volume                     2707.58(13)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13755
_diffrn_reflns_theta_full        76.653
_diffrn_reflns_theta_max         76.653
_diffrn_reflns_theta_min         3.224
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1167.994
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 2288 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.0004106
_refine_ls_shift/su_mean         0.0000546
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.62P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0950
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0949
_reflns_limit_h_max              17
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              -34
_reflns_number_gt                4983
_reflns_number_total             5388
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      0.04
_oxford_refine_ls_r_factor_ref   0.0390
_oxford_refine_ls_scale          5.25(7)
_oxford_reflns_number_all        5387
_oxford_structure_analysis_title 7002
_cod_data_source_file            d1sc04247e2.cif
_cod_data_source_block           7002
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P c a 21 '
_cod_database_code               1564697
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  -0.07(9)
_oxford_bijvoet_difference       -0.05(9)
_oxford_refined_flack_x          -0.03(15)