Metal-free cyclization of unsaturated hydrazones for the divergent assembly of pyrazolones and pyrazolines.
Liu, Xiaobing; Zhou, Yao; Song, Qiuling; Chemical communications (Cambridge, England) 55 (2019) 8943–8946; doi:10.1039/c9cc04039k

data_7125767
_publ_section_title
;
 Metal-free cyclization of unsaturated hydrazones for the divergent
 assembly of pyrazolones and pyrazolines.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8943
_journal_page_last               8946
_journal_paper_doi               10.1039/c9cc04039k
_journal_volume                  55
_journal_year                    2019
_chemical_formula_moiety         'C18 H17 N3 O4'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.35
_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_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc20zy65
_audit_creation_date             2018-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-11-02 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.444(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9361(7)
_cell_length_b                   26.091(3)
_cell_length_c                   10.7999(11)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.0170
_cell_measurement_theta_min      3.8670
_cell_volume                     1654.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -12.00  71.00   1.00    9.00    --   15.65   0.00 -30.00   83
  2  \w     -6.00  20.00   1.00    9.00    --  -16.43 -99.00-120.00   26
  3  \w    -13.00  31.00   1.00    9.00    --   15.65 -57.00 -30.00   44
  4  \w    -24.00  15.00   1.00    9.00    --  -16.43 -99.00  60.00   39
  5  \w     49.00  74.00   1.00    9.00    --   15.65 178.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221301000
_diffrn_orient_matrix_UB_12      -0.0266134000
_diffrn_orient_matrix_UB_13      0.0041456000
_diffrn_orient_matrix_UB_21      0.0569587000
_diffrn_orient_matrix_UB_22      -0.0045942000
_diffrn_orient_matrix_UB_23      -0.0522054000
_diffrn_orient_matrix_UB_31      0.1041875000
_diffrn_orient_matrix_UB_32      -0.0031839000
_diffrn_orient_matrix_UB_33      0.0408107000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7744
_diffrn_reflns_theta_full        24.9991
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3622
_exptl_crystal_description       block
_exptl_crystal_F_000             712.3781
_refine_diff_density_max         0.3181
_refine_diff_density_min         -0.3807
_refine_diff_density_rms         0.0669
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7285
_refine_ls_goodness_of_fit_ref   1.0831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0831
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.5823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1542
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -7
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -5
_reflns_number_gt                2078
_reflns_number_total             2898
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9cc04039k2.cif
_cod_data_source_block           exp_6020
_cod_original_cell_volume        1654.6(3)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7125767
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00N(H00a,H00b,H00c), C00P(H00f,H00n,H00p)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.503