Tandem Oxidative Dearomatizing Spirocyclizations of Propargyl Guanidines and Ureas.
Singh, Ravi P.; Das, Jayanta; Yousufuddin, Muhammed; Gout, Delphine; Lovely, Carl J.; Organic letters 19 (2017) 4110–4113; doi:10.1021/acs.orglett.7b01898

data_1547118
_publ_section_title
;
 Tandem Oxidative Dearomatizing Spirocyclizations of Propargyl Guanidines
 and Ureas.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4110
_journal_page_last               4113
_journal_paper_doi               10.1021/acs.orglett.7b01898
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C25 H21 N2 O3'
_chemical_formula_sum            'C25 H21 N2 O3'
_chemical_formula_weight         397.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6628(17)
_cell_length_b                   18.241(3)
_cell_length_c                   11.829(2)
_cell_measurement_reflns_used    5101
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      2.94
_cell_volume                     2085.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16662
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_min         2.942
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       prism
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.632
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0836P)^2^+1.2156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2869
_reflns_number_total             3655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01898_si_005.cif
_cod_data_source_block           cpd31
_cod_original_cell_volume        2084.9(6)
_cod_database_code               1547118
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              87358
_shelx_hkl_checksum              92510