Intramolecular oxonium ylide formation-[2,3] sigmatropic rearrangement of diazocarbonyl-substituted cyclic unsaturated acetals: a formal synthesis of hyperolactone C.
Hodgson, David M.; Man, Stanislav; Powell, Kimberley J.; Perko, Ziga; Zeng, Minxiang; Moreno-Clavijo, Elena; Thompson, Amber L.; Moore, Michael D.; The Journal of organic chemistry 79 (2014) 9728–9734; doi:10.1021/jo501893r

data_4030004
_publ_section_title
;
 Intramolecular oxonium ylide formation-[2,3] sigmatropic rearrangement of
 diazocarbonyl-substituted cyclic unsaturated acetals: a formal synthesis
 of hyperolactone C.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9728
_journal_page_last               9734
_journal_paper_doi               10.1021/jo501893r
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C9 H8 O4'
_chemical_formula_sum            'C9 H8 O4'
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_chemical_melting_point          ?
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_symmetry_space_group_name_Hall  '-P 1'
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_audit_creation_date             11-09-05
_audit_creation_method           CRYSTALS_ver_14.23
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_cell_angle_gamma                66.739(3)
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_cell_length_c                   9.3705(3)
_cell_measurement_reflns_used    15389
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     422.06(2)
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_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
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_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3318
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_diffrn_reflns_theta_max         76.498
_diffrn_reflns_theta_min         4.735
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_exptl_crystal_density_meas      ?
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_exptl_crystal_size_mid          0.180
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_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       32(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         1768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.0004092
_refine_ls_shift/su_mean         0.0000573
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.13P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0726
_refine_ls_wR_factor_gt          0.0721
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_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1719
_reflns_number_total             1768
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.18
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0294
_oxford_refine_ls_scale          17.1(14)
_oxford_reflns_number_all        1768
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6319
_cod_data_source_file            jo501893r_si_002.cif
_cod_data_source_block           8a
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_symmetry_cell_setting' value
'Triclinic' changed to 'triclinic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030004.cif.

The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4030004
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 102,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;