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#$Date: 2020-09-06 02:37:42 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255932 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038733.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038733
loop_
_publ_author_name
'Marchenko, Anatoliy'
'Koidan, Georgyi'
'Hurieva, Anastasiia N.'
'Shishkina, Svitlana'
'Rusanov, Eduard'
'Kostyuk, Aleksandr'
_publ_section_title
;
 Ring Enlargement of N-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_absolute_configuration ad
_chemical_formula_moiety         'C23 H34 N5 P'
_chemical_formula_sum            'C23 H34 N5 P'
_chemical_formula_weight         411.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 111.6950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4743(2)
_cell_length_b                   16.7492(3)
_cell_length_c                   9.7420(2)
_cell_measurement_reflns_used    7523
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.25
_cell_volume                     1133.20(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Smart Apex II'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17658
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         2.250
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.7322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0418P)²+0.1067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0785
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                4263
_reflns_number_total             4567
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00750_si_004.cif
_cod_data_source_block           kg26
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038733
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4043(3) 0.57930(13) 0.6890(3) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.4048(4) 0.50105(15) 0.6388(3) 0.0218(5) Uani 1 1 d . . . . .
H2 H 0.315720 0.486690 0.546690 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5337(4) 0.44464(16) 0.7223(3) 0.0267(6) Uani 1 1 d . . . . .
H3 H 0.529728 0.392943 0.686503 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6685(4) 0.46464(15) 0.8589(3) 0.0290(6) Uani 1 1 d . . . . .
H4 H 0.756966 0.427019 0.914846 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6698(4) 0.54156(16) 0.9113(3) 0.0263(6) Uani 1 1 d . . . . .
H5 H 0.760251 0.555017 1.003427 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5400(3) 0.59932(15) 0.8302(3) 0.0198(5) Uani 1 1 d . . . . .
C7 C 0.5472(3) 0.68199(16) 0.8919(3) 0.0225(5) Uani 1 1 d . . . . .
H7A H 0.677905 0.693361 0.958007 0.027 Uiso 1 1 calc R U . . .
H7B H 0.513330 0.720193 0.811427 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2189(3) 0.67301(14) 0.8881(2) 0.0199(5) Uani 1 1 d . . . . .
H8A H 0.146746 0.677655 0.952494 0.024 Uiso 1 1 calc R U . . .
H8B H 0.213309 0.617519 0.858257 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4402(4) 0.77143(17) 1.0405(3) 0.0313(6) Uani 1 1 d . . . . .
H9A H 0.360325 0.775459 1.097930 0.047 Uiso 1 1 calc R U . . .
H9B H 0.403219 0.811612 0.964850 0.047 Uiso 1 1 calc R U . . .
H9C H 0.572468 0.779088 1.103465 0.047 Uiso 1 1 calc R U . . .
C10 C -0.1255(3) 0.63211(16) 0.5109(3) 0.0244(6) Uani 1 1 d . . . . .
C11 C -0.0964(4) 0.55797(18) 0.6095(3) 0.0349(7) Uani 1 1 d . . . . .
H11A H 0.012600 0.528263 0.607782 0.052 Uiso 1 1 calc R U . . .
H11B H -0.074146 0.574259 0.708945 0.052 Uiso 1 1 calc R U . . .
H11C H -0.209401 0.525050 0.573424 0.052 Uiso 1 1 calc R U . . .
C12 C -0.1646(4) 0.6050(2) 0.3521(3) 0.0391(7) Uani 1 1 d . . . . .
H12A H -0.054730 0.576504 0.348957 0.059 Uiso 1 1 calc R U . . .
H12B H -0.275241 0.570597 0.319291 0.059 Uiso 1 1 calc R U . . .
H12C H -0.188409 0.650791 0.288657 0.059 Uiso 1 1 calc R U . . .
C13 C -0.3001(4) 0.67754(19) 0.5168(3) 0.0356(7) Uani 1 1 d . . . . .
H13A H -0.274913 0.694404 0.616429 0.053 Uiso 1 1 calc R U . . .
H13B H -0.324054 0.723460 0.453589 0.053 Uiso 1 1 calc R U . . .
H13C H -0.410887 0.643266 0.484222 0.053 Uiso 1 1 calc R U . . .
C14 C 0.1149(3) 0.77644(15) 0.4706(3) 0.0215(5) Uani 1 1 d . . . . .
C15 C 0.1666(4) 0.74667(17) 0.3402(3) 0.0301(6) Uani 1 1 d . . . . .
H15A H 0.284542 0.716822 0.377277 0.045 Uiso 1 1 calc R U . . .
H15B H 0.065200 0.713076 0.277601 0.045 Uiso 1 1 calc R U . . .
H15C H 0.182425 0.791577 0.284463 0.045 Uiso 1 1 calc R U . . .
C16 C -0.0729(4) 0.82380(17) 0.4097(3) 0.0296(6) Uani 1 1 d . . . . .
H16A H -0.174559 0.789579 0.349345 0.044 Uiso 1 1 calc R U . . .
H16B H -0.104357 0.843990 0.490249 0.044 Uiso 1 1 calc R U . . .
H16C H -0.057689 0.867580 0.351356 0.044 Uiso 1 1 calc R U . . .
C17 C 0.2776(4) 0.83084(17) 0.5670(3) 0.0325(7) Uani 1 1 d . . . . .
H17A H 0.395381 0.800953 0.605056 0.049 Uiso 1 1 calc R U . . .
H17B H 0.293030 0.874623 0.508730 0.049 Uiso 1 1 calc R U . . .
H17C H 0.246362 0.851032 0.647623 0.049 Uiso 1 1 calc R U . . .
C18 C -0.1130(4) 0.87318(14) 0.8709(3) 0.0233(6) Uani 1 1 d . . . . .
C19 C -0.1513(5) 0.9324(2) 0.7636(3) 0.0482(9) Uani 1 1 d . . . . .
H19 H -0.106795 0.927085 0.686663 0.058 Uiso 1 1 calc R U . . .
C20 C -0.2553(5) 0.9988(2) 0.7719(3) 0.0527(10) Uani 1 1 d . . . . .
H20 H -0.280649 1.038384 0.700261 0.063 Uiso 1 1 calc R U . . .
C21 C -0.3228(4) 1.00717(19) 0.8861(3) 0.0374(7) Uani 1 1 d . . . . .
H21 H -0.397227 1.051169 0.889002 0.045 Uiso 1 1 calc R U . . .
C22 C -0.2789(4) 0.95005(17) 0.9948(3) 0.0321(6) Uani 1 1 d . . . . .
H22 H -0.320226 0.956048 1.073312 0.039 Uiso 1 1 calc R U . . .
C23 C -0.1730(4) 0.88359(16) 0.9872(3) 0.0278(6) Uani 1 1 d . . . . .
H23 H -0.141901 0.845454 1.061803 0.033 Uiso 1 1 calc R U . . .
N1 N 0.2822(3) 0.63546(12) 0.5968(2) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.4169(3) 0.69273(13) 0.9725(2) 0.0221(4) Uani 1 1 d . . . . .
N3 N 0.1200(3) 0.72209(12) 0.7533(2) 0.0192(4) Uani 1 1 d . . . . .
N4 N 0.0078(3) 0.78654(12) 0.7524(2) 0.0198(4) Uani 1 1 d . . . . .
N5 N -0.0014(3) 0.80301(12) 0.8757(2) 0.0226(5) Uani 1 1 d . . . . .
P1 P 0.10679(8) 0.68757(3) 0.58342(6) 0.01563(14) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 119.7(2) . . ?
N1 C1 C6 122.2(2) . . ?
C2 C1 C6 117.9(2) . . ?
C3 C2 C1 121.8(2) . . ?
C2 C3 C4 120.3(2) . . ?
C3 C4 C5 119.0(2) . . ?
C4 C5 C6 122.0(3) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 120.0(2) . . ?
C1 C6 C7 120.9(2) . . ?
N2 C7 C6 113.2(2) . . ?
N2 C8 N3 116.47(19) . . ?
C13 C10 C12 109.8(2) . . ?
C13 C10 C11 107.7(2) . . ?
C12 C10 C11 108.8(2) . . ?
C13 C10 P1 115.21(18) . . ?
C12 C10 P1 109.51(18) . . ?
C11 C10 P1 105.61(17) . . ?
C16 C14 C17 109.6(2) . . ?
C16 C14 C15 108.8(2) . . ?
C17 C14 C15 108.3(2) . . ?
C16 C14 P1 114.67(17) . . ?
C17 C14 P1 107.74(16) . . ?
C15 C14 P1 107.49(18) . . ?
C23 C18 C19 119.3(2) . . ?
C23 C18 N5 116.1(2) . . ?
C19 C18 N5 124.4(2) . . ?
C20 C19 C18 119.7(3) . . ?
C19 C20 C21 120.6(3) . . ?
C22 C21 C20 119.6(3) . . ?
C21 C22 C23 119.8(3) . . ?
C18 C23 C22 120.9(3) . . ?
C1 N1 P1 140.93(17) . . ?
C8 N2 C9 113.1(2) . . ?
C8 N2 C7 114.23(18) . . ?
C9 N2 C7 111.2(2) . . ?
N4 N3 C8 123.01(18) . . ?
N4 N3 P1 116.25(15) . . ?
C8 N3 P1 119.63(15) . . ?
N5 N4 N3 114.63(18) . . ?
N4 N5 C18 112.66(19) . . ?
N1 P1 N3 111.37(10) . . ?
N1 P1 C10 113.23(12) . . ?
N3 P1 C10 104.27(11) . . ?
N1 P1 C14 106.87(11) . . ?
N3 P1 C14 107.22(10) . . ?
C10 P1 C14 113.79(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.385(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.414(3) . ?
C2 C3 1.380(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.391(3) . ?
C6 C7 1.503(4) . ?
C7 N2 1.470(3) . ?
C8 N2 1.441(3) . ?
C8 N3 1.493(3) . ?
C9 N2 1.457(3) . ?
C10 C13 1.530(4) . ?
C10 C12 1.533(4) . ?
C10 C11 1.536(4) . ?
C10 P1 1.863(3) . ?
C14 C16 1.528(3) . ?
C14 C17 1.532(4) . ?
C14 C15 1.541(3) . ?
C14 P1 1.865(2) . ?
C18 C23 1.375(4) . ?
C18 C19 1.391(4) . ?
C18 N5 1.432(3) . ?
C19 C20 1.376(4) . ?
C20 C21 1.388(4) . ?
C21 C22 1.374(4) . ?
C22 C23 1.384(4) . ?
N1 P1 1.540(2) . ?
N3 N4 1.365(3) . ?
N3 P1 1.7213(19) . ?
N4 N5 1.259(3) . ?
