Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical exocyclic dienones: Microwave-assisted synthesis of novel mono- and dispiropyrazoline derivatives
gazzeh, houda gazzeh; Boudriga, Sarra; Askri, Moheddine; Khatyr, Abderrahim; Knorr, Michael; Strohman, Carsten; Golz, Christopher; Rousselin, Yoann; Kubicki, Marek; RSC Adv.  (2016) –; doi:10.1039/C6RA09703K

data_7225214
_publ_section_title
;
 Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical
 exocyclic dienones: Microwave-assisted synthesis of novel mono- and
 dispiropyrazoline derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA09703K
_journal_year                    2016
_chemical_formula_moiety         'C52 H42 N4 O3'
_chemical_formula_sum            'C52 H42 N4 O3'
_chemical_formula_weight         770.89
_chemical_name_systematic
4,4''-bis(4-methoxyphenyl)-2,2'',5,5''-tetraphenyl-2,2'',4,4''-tetrahydro-2'H,4'H-dispiro[pyrazole-3,1'-naphthalene-3',3''-pyrazol]-2'-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-31 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.682(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5227(14)
_cell_length_b                   21.1915(17)
_cell_length_c                   15.1214(15)
_cell_measurement_reflns_used    2857
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.8450
_cell_measurement_theta_min      2.4090
_cell_volume                     4501.8(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 16.0560
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7909
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.250
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1624
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         7909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0736
_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^)+(0.0818P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3888
_reflns_number_total             7909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra09703k2.cif
_cod_data_source_block           2904
_cod_database_code               7225214
_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:
 C18(H18), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C41(H41), C42(H42), C44(H44), C45(H45), C48(H48), C49(H49), C50(H50), C51(H51),
  C52(H52)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              67463
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method Chloroform/Ethanol