Formal Synthesis of (±)-Pentalenolactone A Methyl Ester.
Niu, Guang-Hao; Liu, Pin-Heng; Hung, Wei-Chun; Tseng, Ping-Yao; Chuang, Gary Jing; The Journal of organic chemistry 84 (2019) 10172–10182; doi:10.1021/acs.joc.9b01349

data_4033994
_publ_section_title
;
 Formal Synthesis of (+-)-Pentalenolactone A Methyl Ester.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10172
_journal_page_last               10182
_journal_paper_doi               10.1021/acs.joc.9b01349
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C14 H17 O2'
_chemical_formula_weight         217.27
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.433(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6989(2)
_cell_length_b                   14.1778(3)
_cell_length_c                   12.0083(3)
_cell_measurement_reflns_used    4093
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2761
_cell_measurement_theta_min      2.8389
_cell_volume                     1263.48(5)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/4'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11168
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.271
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.1031
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+3.2656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2106
_refine_ls_wR_factor_ref         0.2306
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1957
_reflns_number_total             3092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01349_si_004.cif
_cod_data_source_block           ghn424_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' 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 21/n'
_cod_database_code               4033994
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              54720
_shelx_hkl_checksum              75366