Rhodium-Catalyzed Intermolecular Carbonylative [2 + 2 + 1] Cycloaddition of Alkynes Using Alcohol as the Carbon Monoxide Source for the Formation of Cyclopentenones.
Kim, Ju Hyun; Song, Taemoon; Chung, Young Keun; Organic letters 19 (2017) 1248–1251; doi:10.1021/acs.orglett.7b00458

data_1545429
_publ_section_title
;
 Rhodium-Catalyzed Intermolecular Carbonylative [2 + 2 + 1] Cycloaddition
 of Alkynes Using Alcohol as the Carbon Monoxide Source for the Formation
 of Cyclopentenones.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1248
_journal_page_last               1251
_journal_paper_doi               10.1021/acs.orglett.7b00458
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8946(9)
_cell_length_b                   18.6719(14)
_cell_length_c                   7.5647(5)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    223
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.77
_cell_volume                     1680.1(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      223.15
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            68162
_diffrn_reflns_theta_full        28.3252
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1207 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.9409.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2666
_exptl_crystal_description       Needle
_exptl_crystal_F_000             680.3520
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.1928
_refine_diff_density_min         -0.2396
_refine_diff_density_rms         0.0470
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.2(11)
_refine_ls_d_res_high            0.7490
_refine_ls_d_res_low             9.3360
_refine_ls_goodness_of_fit_ref   0.9101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9101
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+1.0340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.998
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              24
_reflns_limit_k_min              -24
_reflns_limit_l_max              10
_reflns_limit_l_min              -10
_reflns_number_gt                3194
_reflns_number_total             4176
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol7b00458_si_002.cif
_cod_data_source_block           CompoundB
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_Hall     ' P 2c -2ac'
_cod_database_code               1545429
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C11(H11), C13(H13), C15(H15), C17(H17), C19(H19), C20(H20),
 C21(H21)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C18(H18a,H18b,H18c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'