Mechanistic Studies on the Base-Promoted Conversion of Alkoxy-Substituted, Ring-Fused gem-Dihalocyclopropanes into Furans: Evidence for a Process Involving Electrocyclic Ring Closure of a Carbonyl Ylide Intermediate.
Sharp, Phillip P.; Mikusek, Jiri; Ho, Junming; Krenske, Elizabeth H.; Banwell, Martin G.; Coote, Michelle L.; Ward, Jas S.; Willis, Anthony C.; The Journal of organic chemistry 83 (2018) 13678–13690; doi:10.1021/acs.joc.8b01766

data_4034860
_publ_section_title
;
 Mechanistic Studies on the Base-Promoted Conversion of
 Alkoxy-Substituted, Ring-Fused gem-Dihalocyclopropanes into Furans:
 Evidence for a Process Involving Electrocyclic Ring Closure of a Carbonyl
 Ylide Intermediate.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13678
_journal_page_last               13690
_journal_paper_doi               10.1021/acs.joc.8b01766
_journal_volume                  83
_journal_year                    2018
_chemical_compound_source        local
_chemical_formula_moiety         'C9 H11 Cl3 O'
_chemical_formula_sum            'C9 H11 Cl3 O'
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_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
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_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-10-04
_audit_creation_method           CRYSTALS_ver_12.18
_audit_update_record
;
2006-10-04 - Report on C9 H11 Cl3 O'
             by Anthony C. Willis
             for   Pat Sharp and Martin Banwell

2006-10-05 - passes checkcif tests with no warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4239(4)
_cell_length_b                   16.5510(7)
_cell_length_c                   7.5180(3)
_cell_measurement_reflns_used    23218
_cell_measurement_temperature    200
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     1048.19(8)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Watkin et al 2003)'
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_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
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_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_number            12245
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_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            yellow
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_refine_ls_abs_structure_details 'Flack (1983), 1072 Friedel-pairs'
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_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          0.001336
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, 
 (Carruthers & Watkin, 1979, Prince, 1982)  
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.917 0.0432 0.651 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0281
_refine_ls_wR_factor_gt          0.0263
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_reflns_limit_h_max              10
_reflns_limit_h_min              0
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -9
_reflns_number_gt                2096
_reflns_number_total             2366
_reflns_threshold_expression     I>3.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.73
_oxford_diffrn_Wilson_scale      0.78
_oxford_refine_ls_scale          1.1661(17)
_oxford_structure_analysis_title 'ban0633 - axes transformed'
_cod_data_source_file            jo8b01766_si_003.cif
_cod_data_source_block           ban0633
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P n a 21 '
_cod_database_code               4034860