Phosphine- and water-promoted pentannulative aldol reaction.
Satpathi, Bishnupada; Dutta, Lona; Ramasastry, S. S. V.; Organic & biomolecular chemistry 17 (2019) 1547–1551; doi:10.1039/c8ob03106a

data_7156655
_publ_section_title
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 Phosphine- and water-promoted pentannulative aldol reaction.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1547
_journal_page_last               1551
_journal_paper_doi               10.1039/c8ob03106a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C21 H20 O2'
_chemical_formula_sum            'C21 H20 O2'
_chemical_formula_weight         304.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_audit_update_record
;
2018-09-01 deposited with the CCDC.
2019-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.294(8)
_cell_angle_beta                 92.253(9)
_cell_angle_gamma                96.879(8)
_cell_formula_units_Z            2
_cell_length_a                   6.299(4)
_cell_length_b                   11.213(7)
_cell_length_c                   12.297(8)
_cell_measurement_reflns_used    4325
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      2.42
_cell_volume                     860.8(9)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10039
_diffrn_reflns_theta_full        24.8927
_diffrn_reflns_theta_max         24.89
_diffrn_reflns_theta_min         1.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0569 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.9188.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.1744
_exptl_crystal_description       block
_exptl_crystal_F_000             324.1541
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.1714
_refine_diff_density_min         -0.1887
_refine_diff_density_rms         0.0368
_refine_ls_d_res_high            0.8443
_refine_ls_d_res_low             12.2748
_refine_ls_goodness_of_fit_ref   1.0631
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0631
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.1392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2437
_reflns_number_total             3003
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob03106a2.cif
_cod_data_source_block           PD_H2L_0m
_cod_depositor_comments          'Adding full bibliography for 7156655.cif.'
_cod_original_cell_volume        860.7(9)
_cod_database_code               7156655
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1a), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
  C15(H15), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'