Ring Enlargement of <i>N</i>-Phosphanyl-1,2,3,4-tetrahydroquinazolines.
Marchenko, Anatoliy; Koidan, Georgyi; Hurieva, Anastasiia N.; Shishkina, Svitlana; Rusanov, Eduard; Kostyuk, Aleksandr; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00750

data_4038732
_publ_section_title
;
 Ring Enlargement of <i>N</i>-Phosphanyl-1,2,3,4-tetrahydroquinazolines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00750
_journal_year                    2020
_chemical_formula_moiety         'C24 H36 N5 P'
_chemical_formula_sum            'C24 H36 N5 P'
_chemical_formula_weight         425.55
_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             2016-02-04
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.509(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7479(4)
_cell_length_b                   13.1447(4)
_cell_length_c                   16.1419(6)
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    294
_cell_measurement_theta_max      28.0100
_cell_measurement_theta_min      3.5970
_cell_volume                     2363.74(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -45.00   42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3583   19.0000  -60.0000 87

  2 omega  -52.00   40.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3583   77.0000  150.0000 92

  3 omega    2.00   42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3583   57.0000  -60.0000 40

  4 omega  -33.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3583  -57.0000  150.0000 26

  5 omega  -92.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3583  -77.0000   30.0000 96

  6 omega   48.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  178.0000  150.0000 26

  7 omega   19.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -99.0000  -90.0000 49

  8 omega   -3.00   23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   77.0000   30.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0572513000
_diffrn_orient_matrix_UB_12      -0.0020842000
_diffrn_orient_matrix_UB_13      0.0323710000
_diffrn_orient_matrix_UB_21      0.0049789000
_diffrn_orient_matrix_UB_22      0.0536651000
_diffrn_orient_matrix_UB_23      -0.0020513000
_diffrn_orient_matrix_UB_31      -0.0273845000
_diffrn_orient_matrix_UB_32      0.0053675000
_diffrn_orient_matrix_UB_33      0.0330930000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19885
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.080
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0526P)^2^+0.4445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4196
_reflns_number_total             5417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00750_si_005.cif
_cod_data_source_block           kost3
_cod_original_cell_volume        2363.75(15)
_cod_database_code               4038732
_reflns_odcompleteness_completeness 90.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.21
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'