Elucidating Latent Mechanistic Complexity in Competing Acid-Catalyzed Reactions of Salicylaldehyde-Derived Baylis-Hillman Adducts.
Olomola, Temitope O.; Klein, Rosalyn; Caira, Mino R.; Kaye, Perry T.; The Journal of organic chemistry 81 (2016) 109–120; doi:10.1021/acs.joc.5b02372

data_4036513
_publ_section_title
;
 Elucidating Latent Mechanistic Complexity in Competing Acid-Catalyzed
 Reactions of Salicylaldehyde-Derived Baylis-Hillman Adducts.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              109
_journal_page_last               120
_journal_paper_doi               10.1021/acs.joc.5b02372
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C10 H9 Cl O3'
_chemical_formula_sum            'C10 H9 Cl O3'
_chemical_formula_weight         212.62
_chemical_melting_point          403.1(10)
_chemical_name_common            none
_chemical_name_systematic
; 
 (Z)-2-(chloromethyl)-3-(2-hydroxyphenyl)-2-propenoic acid 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.256(4)
_cell_angle_beta                 91.114(7)
_cell_angle_gamma                100.217(7)
_cell_formula_units_Z            2
_cell_length_a                   5.1208(4)
_cell_length_b                   7.8498(8)
_cell_length_c                   11.9863(12)
_cell_measurement_reflns_used    2115
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     467.43(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT 2000'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean n/a
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       'phi- and omega-scans of 1.00 deg.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25716
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.42
_diffrn_standards_decay_%        n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_correction_T_min  0.8653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (sheldrick, 1996)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0765
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1184P)^2^+0.7230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2285
_reflns_number_gt                1552
_reflns_number_total             2115
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02372_si_003.cif
_cod_data_source_block           c:\to18as
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '129-131C' was changed to
'403.1(10)' -- it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               4036513