Phosphine-catalyzed [4 + 2] cycloaddition of unsaturated pyrazolones with allenoates: a concise approach toward spiropyrazolones
Yang, Wenjun; Zhang, Yunpeng; Qiu, Shuxian; Zhao, Chuanqi; Zhang, Lei; Liu, Honglei; Zhou, Leijie; Xiao, Yumei; Guo, Hongchao; RSC Adv. 5 (2015) 62343–; doi:10.1039/C5RA11595G

data_7221602
_publ_section_title
;
 Phosphine-catalyzed [4 + 2] cycloaddition of unsaturated pyrazolones with
 allenoates: a concise approach toward spiropyrazolones
;
_journal_issue                   77
_journal_name_full               'RSC Adv.'
_journal_page_first              62343
_journal_paper_doi               10.1039/C5RA11595G
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H27 Cl N2 O5'
_chemical_formula_sum            'C27 H27 Cl N2 O5'
_chemical_formula_weight         494.95
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-06-16 deposited with the CCDC.
2015-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.513(2)
_cell_length_b                   13.093(3)
_cell_length_c                   17.827(4)
_cell_measurement_reflns_used    8059
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4809
_cell_measurement_theta_min      1.9298
_cell_volume                     2453.8(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0288
_diffrn_orient_matrix_UB_12      0.0478
_diffrn_orient_matrix_UB_13      0.0770
_diffrn_orient_matrix_UB_21      0.0716
_diffrn_orient_matrix_UB_22      -0.0003
_diffrn_orient_matrix_UB_23      -0.0267
_diffrn_orient_matrix_UB_31      -0.0097
_diffrn_orient_matrix_UB_32      0.0485
_diffrn_orient_matrix_UB_33      -0.0265
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.930
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4908
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.546
_exptl_crystal_size_min          0.518
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0464P)^2^+0.4182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5578
_reflns_number_total             5618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra11595g2.cif
_cod_data_source_block           sa3329
_cod_original_cell_volume        2453.9(9)
_cod_database_code               7221602
_shelxl_version_number           2013-4
_diffrn_number_total             3191
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C23(H23A,H23B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              60954
_shelx_hkl_checksum              64144