Catalyst-Free Rearrangement of Allenyl Aryldiazoacetates into 1,5-Dihydro-4H-pyrazol-4-ones.
Marichev, Kostiantyn O.; Qiu, Huang; Offield, Austin C.; Arman, Hadi; Doyle, Michael P.; The Journal of organic chemistry 81 (2016) 9235–9246; doi:10.1021/acs.joc.6b01833

data_4037240
_publ_section_title
;
 Catalyst-Free Rearrangement of Allenyl Aryldiazoacetates into
 1,5-Dihydro-4H-pyrazol-4-ones.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9235
_journal_page_last               9246
_journal_paper_doi               10.1021/acs.joc.6b01833
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H18 N2 O2'
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.297(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.920(7)
_cell_length_b                   6.022(2)
_cell_length_c                   15.745(6)
_cell_measurement_reflns_used    6051
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.6
_cell_volume                     1676.8(11)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
	Number of images: 330
	           Slice: -125.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 65.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 34.9985
	          2theta: -34.9790
scan:
	Number of images: 102
	           Slice: -68.0000 - -17.0000
	     Image width: 0.5000
	        Exp time: 65.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.9985
	          2theta: -34.9790
scan:
	Number of images: 78
	           Slice: -68.0000 - -29.0000
	     Image width: 0.5000
	        Exp time: 65.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 34.9985
	          2theta: -34.9790
scan:
	Number of images: 60
	           Slice: -55.0000 - -25.0000
	     Image width: 0.5000
	        Exp time: 65.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.9985
	          2theta: -34.9790
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.000895
_diffrn_orient_matrix_UB_12      -0.041344
_diffrn_orient_matrix_UB_13      -0.049311
_diffrn_orient_matrix_UB_21      -0.166023
_diffrn_orient_matrix_UB_22      0.000406
_diffrn_orient_matrix_UB_23      -0.003352
_diffrn_orient_matrix_UB_31      0.000955
_diffrn_orient_matrix_UB_32      0.036896
_diffrn_orient_matrix_UB_33      -0.042839
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_unetI/netI     0.1292
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8256
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.622
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0785
_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^)+(0.0100P)^2^+6.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1994
_reflns_number_total             2953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01833_si_003.cif
_cod_data_source_block           cd1309a
_cod_database_code               4037240
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C10(H10), C11(H11), C14(H14), C17(H17), C13(H13), C21(H21),
 C5(H5), C18(H18), C20(H20), C19(H19)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'