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_7221600
_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_formula_moiety         'C27 H27 Br N2 O5'
_chemical_formula_sum            'C27 H27 Br N2 O5'
_chemical_formula_weight         539.41
_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_date             2014-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-06-16 deposited with the CCDC.
2015-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.779(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.786(2)
_cell_length_b                   16.7779(19)
_cell_length_c                   35.405(4)
_cell_measurement_reflns_used    14901
_cell_measurement_temperature    223.1500
_cell_measurement_theta_max      27.4851
_cell_measurement_theta_min      1.7171
_cell_volume                     9960(2)
_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., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      223.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0097
_diffrn_orient_matrix_UB_12      0.0517
_diffrn_orient_matrix_UB_13      -0.0280
_diffrn_orient_matrix_UB_21      -0.0087
_diffrn_orient_matrix_UB_22      0.0293
_diffrn_orient_matrix_UB_23      0.0511
_diffrn_orient_matrix_UB_31      0.0278
_diffrn_orient_matrix_UB_32      -0.0008
_diffrn_orient_matrix_UB_33      0.0052
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            33600
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         1.717
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       Plate
_exptl_crystal_F_000             4448
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 5679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.044(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1273
_refine_ls_number_reflns         20699
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+7.9780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                17351
_reflns_number_total             20699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra11595g2.cif
_cod_data_source_block           mx3424
_cod_original_cell_volume        9959(2)
_cod_database_code               7221600
_shelxl_version_number           2013-4
_diffrn_number_total             11781
_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:
 C1C(H1C), C3C(H3C), C1B(H1B), C3B(H3B), C1(H1), C3(H3), C1A(H1A), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C4C(H4CA,H4CB), C8C(H8CA,H8CB), C26C(H26A,H26B), C4B(H4BA,H4BB), C8B(H8BA,
 H8BB), C26B(H26C,H26D), C4(H4A,H4B), C8(H8A,H8B), C26(H26E,H26F), C4A(H4AA,
 H4AB), C8A(H8AA,H8AB), C26A(H26G,H26H)
2.c Aromatic/amide H refined with riding coordinates:
 C5C(H5C), C14C(H14C), C15C(H15C), C16C(H16C), C17C(H17C), C18C(H18C),
 C20C(H20C), C22C(H22C), C23C(H23C), C24C(H24C), C5B(H5B), C14B(H14B),
 C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B), C20B(H20B), C22B(H22B),
 C23B(H23B), C24B(H24B), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C22(H22), C23(H23), C24(H24), C5A(H5A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A), C20A(H20A), C22A(H22A),
 C23A(H23A), C24A(H24A)
2.d Idealised Me refined as rotating group:
 C9C(H9CA,H9CB,H9CC), C12C(H12A,H12B,H12C), C27C(H27A,H27B,H27C), C9B(H9BA,
 H9BB,H9BC), C12B(H12D,H12E,H12F), C27B(H27D,H27E,H27F), C9(H9A,H9B,H9C),
 C12(H12G,H12H,H12I), C27(H27G,H27H,H27I), C9A(H9AA,H9AB,H9AC), C12A(H12J,H12K,
 H12L), C27A(H27J,H27K,H27L)
;
_shelx_res_checksum              75682
_shelx_hkl_checksum              8167