Synthesis of Pyrano[3,2-c]pyrazol-7(1H)-one Derivatives by Tandem Cyclization of 2-Diazo-3,5-dioxo-6-ynoates (Ynones).
Deng, Guisheng; Wang, Feng; Lu, Shengle; Cheng, Bo; Organic letters 17 (2015) 4651–4653; doi:10.1021/acs.orglett.5b02369

data_1555306
_publ_section_title
;
 Synthesis of Pyrano[3,2-c]pyrazol-7(1H)-one Derivatives by Tandem
 Cyclization of 2-Diazo-3,5-dioxo-6-ynoates (Ynones).
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4651
_journal_page_last               4653
_journal_paper_doi               10.1021/acs.orglett.5b02369
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C18 H18 N2 O4'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2015-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.475(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3073(3)
_cell_length_b                   12.3863(2)
_cell_length_c                   11.7620(2)
_cell_measurement_temperature    293
_cell_volume                     1601.99(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  supernova
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.985
_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       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8583
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         5.264
_exptl_absorpt_coefficient_mu    0.797
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          2.0
_exptl_crystal_size_mid          2.0
_exptl_crystal_size_min          2.0
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0020(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0891P)^2^+0.2569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2545
_reflns_number_total             2854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02369_si_002.cif
_cod_data_source_block           exp_15
_cod_database_code               1555306
_shelxl_version_number           2014-1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00L(H00C,H00D), C00N(H00M,H00N)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J)
2.c Idealised Me refined as rotating group:
 C00M(H00G,H00K,H00L), C00O(H00O,H00P,H00Q)
;
_shelx_res_checksum              73226
_shelx_hkl_checksum              34399
_olex2_submission_special_instructions 'No special instructions were received'