Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles generated highly substituted cyclopentenes through an unexpected phosphine α-addition-δ-evolvement of an anion pathway.
Chuang, Shih-Ching; Sung, Shih-Ping; Deng, Jie-Cheng; Chiou, Mong-Feng; Hsu, Day-Shin; Organic & biomolecular chemistry 14 (2016) 2306–2317; doi:10.1039/c5ob02445e

data_7154897
_publ_section_title
;
 Multicomponent reactions of phosphines, enynedioates and benzylidene
 malononitriles generated highly substituted cyclopentenes through an
 unexpected phosphine \a-addition-\d-evolvement of an anion pathway.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2306
_journal_page_last               2317
_journal_paper_doi               10.1039/c5ob02445e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C36 H28 N3 O6 P'
_chemical_formula_weight         629.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-02-24 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.461(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.087(3)
_cell_length_b                   21.192(5)
_cell_length_c                   12.419(3)
_cell_measurement_reflns_used    7916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.5149
_cell_measurement_theta_min      2.4775
_cell_volume                     3175.3(13)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12751
_diffrn_reflns_point_group_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.589
_diffrn_reflns_theta_min         1.922
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+1.1097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.645
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                5152
_reflns_number_total             5289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02445e2.cif
_cod_data_source_block           publication_text
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154897--7154898.cif.
;
_cod_database_code               7154897
_shelxl_version_number           2014/6
_shelx_res_checksum              14456