The first example of the stereoselective synthesis and crystal structure of a spirobicycloquinazolinone based on (–)-fenchone and anthranilamide
Chernyshov, Vladimir V.; Gatilov, Yuri V.; Yarovaya, Olga I.; Koskin, Igor P.; Yarovoy, Spartak S.; Brylev, Konstantin A.; Salakhutdinov, Nariman F.; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619015766

data_2021839
_publ_section_title
;
 The first example of the stereoselective synthesis and crystal structure
 of a spirobicycloquinazolinone based on (--)-fenchone and anthranilamide
;
_journal_coeditor_code           VP3001
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619015766
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C17 H22 N2 O'
_chemical_formula_moiety         'C17 H22 N2 O'
_chemical_formula_sum            'C17 H22 N2 O'
_chemical_formula_weight         270.36
_chemical_name_common
;
Spiro[fench-2,2'-(2,3-dihydro-1<i>H</i>-quinazolin-4-one)]
;
_chemical_name_systematic
(1<i>R</i>,2<i>S</i>,4<i>S</i>)-1,3,3-Trimethyl-1'<i>H</i>-spiro[bicyclo[2.2.1]heptane-2,2'-quinazolin]-4'(3'<i>H</i>)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8870(5)
_cell_length_b                   12.2535(5)
_cell_length_c                   27.7511(11)
_cell_measurement_reflns_used    7659
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.47
_cell_measurement_theta_min      2.26
_cell_volume                     4042.2(3)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2008)
;
_computing_publication_material
;
SHELXTL (Bruker, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32223
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.691
_diffrn_reflns_theta_min         1.468
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_correction_T_min  0.8014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS, Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.889
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.165
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1849 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   2.7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         7494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0542
_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^)+(0.1152P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1777
_reflns_number_gt                5139
_reflns_number_total             7494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vp3001sup1.cif
_cod_data_source_block           I
_cod_database_code               2021839
_cod_database_fobs_code          2021839
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.989
_shelx_hkl_checksum              74953
_shelx_res_checksum              53109
_shelx_fab_checksum              38060