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#$Date: 2022-01-24 11:01:39 +0200 (Mon, 24 Jan 2022) $
#$Revision: 272210 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566109.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_1566109
loop_
_publ_author_name
'Guillon, Jean'
'Rubio, Sandra'
'Savrimoutou, Solène'
'Hallé, François'
'Moreau, Stéphane'
'Sonnet, Pascal'
'Marchivie, Mathieu'
_publ_section_title
;
 Crystal structure and identification of a
 pyrimido[6,1-b][1,3]oxazin-6-one derivative from the reaction of acrolein
 with 5-(phenoxymethyl)-2-amino-2-oxazoline
;
_journal_issue                   11
_journal_name_full               'Comptes Rendus Chimie'
_journal_page_first              987
_journal_page_last               992
_journal_paper_doi               10.1016/j.crci.2018.09.013
_journal_volume                  21
_journal_year                    2018
_chemical_formula_sum            'C26 H32 N4 O6'
_chemical_formula_weight         496.56
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.041(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3337(10)
_cell_length_b                   11.3712(7)
_cell_length_c                   10.4936(7)
_cell_measurement_reflns_used    4497
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      72.31
_cell_measurement_theta_min      2.13
_cell_volume                     2480.0(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku RAXIS Rapid'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'Rigaku VariMax mirror'
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            32457
_diffrn_reflns_theta_full        72.31
_diffrn_reflns_theta_max         72.31
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  0.8912
_exptl_absorpt_correction_T_min  0.8586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4802
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0920P)²+0.6898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1878
_reflns_number_gt                4497
_reflns_number_total             4802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            CRC-2018-21-987.CIF
_cod_data_source_block           jg504
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1566109
_symmetry_absolute_configuration ad
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41648(9) 0.2122(2) 0.6955(2) 0.0518(5) Uani 1 1 d . . .
C2 C 0.41118(13) 0.1289(2) 0.7881(3) 0.0657(7) Uani 1 1 d . . .
H2 H 0.3792 0.1361 0.8376 0.079 Uiso 1 1 calc R . .
C3 C 0.45351(16) 0.0341(3) 0.8077(3) 0.0782(8) Uani 1 1 d . . .
H3 H 0.4505 -0.0230 0.8722 0.094 Uiso 1 1 calc R . .
C4 C 0.49911(14) 0.0215(3) 0.7367(3) 0.0758(8) Uani 1 1 d . . .
H4 H 0.5277 -0.0437 0.7513 0.091 Uiso 1 1 calc R . .
C5 C 0.50329(12) 0.1034(3) 0.6443(3) 0.0711(7) Uani 1 1 d . . .
H5 H 0.5348 0.0945 0.5939 0.085 Uiso 1 1 calc R . .
C6 C 0.46257(11) 0.1986(2) 0.6228(3) 0.0610(6) Uani 1 1 d . . .
H6 H 0.4661 0.2551 0.5581 0.073 Uiso 1 1 calc R . .
O7 O 0.37896(8) 0.31074(18) 0.66687(18) 0.0728(5) Uani 1 1 d . . .
C8 C 0.33996(12) 0.3477(3) 0.7538(3) 0.0740(8) Uani 1 1 d . B .
H8A H 0.3542 0.4262 0.7898 0.089 Uiso 1 1 calc R . .
H8B H 0.3449 0.2917 0.8277 0.089 Uiso 1 1 calc R . .
C9 C 0.26991(10) 0.35323(19) 0.6818(2) 0.0490(5) Uani 1 1 d D . .
H9 H 0.2545 0.2818 0.6381 0.050 Uiso 0.75 1 d PD A 1
O10 O 0.23402(9) 0.37613(18) 0.7794(2) 0.0506(5) Uani 0.75 1 d P B 1
H10 H 0.2316 0.3143 0.8219 0.076 Uiso 0.75 1 calc PR B 1
H9' H 0.2460 0.3682 0.7465 0.050 Uiso 0.25 1 d PD C 2
O10' O 0.2453(3) 0.2403(5) 0.6113(6) 0.0572(15) Uani 0.25 1 d P B 2
H10' H 0.2516 0.1883 0.6678 0.060 Uiso 0.25 1 d P D 2
C11 C 0.25899(9) 0.45080(19) 0.5809(2) 0.0463(5) Uani 1 1 d . B .
H11A H 0.2691 0.5271 0.6263 0.056 Uiso 1 1 calc R . .
H11B H 0.2891 0.4400 0.5225 0.056 Uiso 1 1 calc R . .
N12 N 0.19323(7) 0.45504(14) 0.50118(16) 0.0398(4) Uani 1 1 d . . .
C13 C 0.18033(9) 0.39884(16) 0.38414(18) 0.0382(4) Uani 1 1 d . B .
N14 N 0.11785(7) 0.39912(13) 0.31127(14) 0.0366(4) Uani 1 1 d . . .
C15 C 0.06394(8) 0.43428(15) 0.36536(18) 0.0374(4) Uani 1 1 d . B .
H15 H 0.0286 0.4637 0.2929 0.045 Uiso 1 1 calc R . .
C16 C 0.08430(9) 0.53186(16) 0.4629(2) 0.0421(4) Uani 1 1 d . . .
H16A H 0.0941 0.6034 0.4173 0.051 Uiso 1 1 calc R B .
H16B H 0.0488 0.5506 0.5062 0.051 Uiso 1 1 calc R . .
C17 C 0.14291(9) 0.49482(17) 0.56384(19) 0.0412(4) Uani 1 1 d . B .
H17A H 0.1589 0.5620 0.6222 0.049 Uiso 1 1 calc R . .
H17B H 0.1313 0.4305 0.6179 0.049 Uiso 1 1 calc R . .
O18 O 0.22379(7) 0.35443(14) 0.33857(16) 0.0545(4) Uani 1 1 d . . .
C19 C 0.09823(10) 0.31058(18) 0.20867(18) 0.0424(4) Uani 1 1 d . B .
H19A H 0.1362 0.2835 0.1773 0.051 Uiso 1 1 calc R . .
H19B H 0.0671 0.3454 0.1337 0.051 Uiso 1 1 calc R . .
C20 C 0.06731(9) 0.20640(17) 0.26301(18) 0.0389(4) Uani 1 1 d . . .
H20A H 0.0482 0.1525 0.1905 0.047 Uiso 1 1 calc R B .
H20B H 0.1009 0.1625 0.3256 0.047 Uiso 1 1 calc R . .
C21 C 0.01541(8) 0.24581(15) 0.33159(16) 0.0337(4) Uani 1 1 d . B .
H21 H -0.0221 0.2774 0.2656 0.040 Uiso 1 1 calc R . .
O22 O 0.04030(6) 0.33673(10) 0.42737(12) 0.0348(3) Uani 1 1 d . . .
N23 N -0.00493(7) 0.14775(13) 0.39761(14) 0.0347(4) Uani 1 1 d . . .
H23 H 0.0221 0.0885 0.4169 0.042 Uiso 1 1 calc R B .
C24 C -0.06165(8) 0.13757(15) 0.43302(17) 0.0340(4) Uani 1 1 d . B .
O25 O -0.10695(6) 0.21924(12) 0.38327(14) 0.0438(4) Uani 1 1 d . . .
C26 C -0.16455(8) 0.18408(18) 0.4269(2) 0.0414(4) Uani 1 1 d . B .
H26 H -0.1777 0.2478 0.4813 0.050 Uiso 1 1 calc R . .
C27 C -0.14338(10) 0.0744(2) 0.5110(2) 0.0531(6) Uani 1 1 d . . .
H27A H -0.1477 0.0873 0.6019 0.064 Uiso 1 1 calc R B .
H27B H -0.1696 0.0054 0.4745 0.064 Uiso 1 1 calc R . .
N28 N -0.07572(7) 0.05670(14) 0.50695(16) 0.0404(4) Uani 1 1 d . B .
C29 C -0.21761(9) 0.16006(18) 0.3096(2) 0.0454(5) Uani 1 1 d . . .
H29A H -0.2030 0.1033 0.2509 0.055 Uiso 1 1 calc R B .
H29B H -0.2552 0.1261 0.3370 0.055 Uiso 1 1 calc R . .
O30 O -0.23475(7) 0.26880(12) 0.24335(14) 0.0481(4) Uani 1 1 d . B .
C31 C -0.28620(9) 0.26774(19) 0.1370(2) 0.0460(5) Uani 1 1 d . . .
C32 C -0.30263(10) 0.3761(2) 0.0784(2) 0.0503(5) Uani 1 1 d . B .
H32 H -0.2791 0.4445 0.1122 0.060 Uiso 1 1 calc R . .
C33 C -0.35348(11) 0.3839(3) -0.0296(2) 0.0620(6) Uani 1 1 d . . .
H33 H -0.3652 0.4581 -0.0695 0.074 Uiso 1 1 calc R B .
C34 C -0.38730(12) 0.2839(3) -0.0798(3) 0.0706(7) Uani 1 1 d . B .
H34 H -0.4218 0.2892 -0.1548 0.085 Uiso 1 1 calc R . .
C35 C -0.37082(12) 0.1775(3) -0.0210(3) 0.0709(7) Uani 1 1 d . . .
H35 H -0.3943 0.1091 -0.0553 0.085 Uiso 1 1 calc R B .
C36 C -0.32021(11) 0.1679(2) 0.0884(2) 0.0594(6) Uani 1 1 d . B .
H36 H -0.3092 0.0938 0.1290 0.071 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O7 C1 C2 125.4(2) . .
O7 C1 C6 115.0(2) . .
C2 C1 C6 119.6(2) . .
C1 C2 C3 118.9(3) . .
C4 C3 C2 121.4(3) . .
C3 C4 C5 119.2(3) . .
C4 C5 C6 121.0(3) . .
C5 C6 C1 119.9(3) . .
C1 O7 C8 119.7(2) . .
O7 C8 C9 110.1(2) . .
O10 C9 C8 106.08(19) . .
O10 C9 C11 110.10(18) . .
C8 C9 C11 110.9(2) . .
O10 C9 O10' 108.7(3) . .
C8 C9 O10' 113.7(3) . .
C11 C9 O10' 107.3(3) . .
N12 C11 C9 113.58(16) . .
C13 N12 C17 122.49(15) . .
C13 N12 C11 118.32(16) . .
C17 N12 C11 117.58(16) . .
O18 C13 N12 121.56(17) . .
O18 C13 N14 119.96(17) . .
N12 C13 N14 118.31(16) . .
C13 N14 C15 122.46(15) . .
C13 N14 C19 119.09(16) . .
C15 N14 C19 110.93(14) . .
O22 C15 N14 110.85(14) . .
O22 C15 C16 109.79(15) . .
N14 C15 C16 109.70(15) . .
C17 C16 C15 109.79(15) . .
N12 C17 C16 110.51(16) . .
N14 C19 C20 109.54(15) . .
C21 C20 C19 111.76(16) . .
N23 C21 O22 108.81(13) . .
N23 C21 C20 109.44(14) . .
O22 C21 C20 110.20(13) . .
C15 O22 C21 110.30(13) . .
C24 N23 C21 126.11(14) . .
N28 C24 N23 125.14(16) . .
N28 C24 O25 118.70(16) . .
N23 C24 O25 116.15(15) . .
C24 O25 C26 105.57(14) . .
O25 C26 C29 108.98(16) . .
O25 C26 C27 104.09(14) . .
C29 C26 C27 113.20(18) . .
N28 C27 C26 104.98(15) . .
C24 N28 C27 106.58(15) . .
O30 C29 C26 107.81(16) . .
C31 O30 C29 117.22(15) . .
O30 C31 C36 124.2(2) . .
O30 C31 C32 115.28(18) . .
C36 C31 C32 120.5(2) . .
C33 C32 C31 119.6(2) . .
C32 C33 C34 120.2(2) . .
C35 C34 C33 119.7(2) . .
C34 C35 C36 120.9(2) . .
C31 C36 C35 119.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O7 1.371(3) .
C1 C2 1.380(4) .
C1 C6 1.382(3) .
C2 C3 1.391(4) .
C3 C4 1.360(4) .
C4 C5 1.361(4) .
C5 C6 1.375(4) .
O7 C8 1.429(3) .
C8 C9 1.516(3) .
C9 O10 1.434(3) .
C9 C11 1.515(3) .
C9 O10' 1.516(6) .
C11 N12 1.463(2) .
N12 C13 1.356(2) .
N12 C17 1.452(2) .
C13 O18 1.242(2) .
C13 N14 1.379(2) .
N14 C15 1.449(2) .
N14 C19 1.465(2) .
C15 O22 1.434(2) .
C15 C16 1.506(3) .
C16 C17 1.505(3) .
C19 C20 1.528(3) .
C20 C21 1.518(2) .
C21 N23 1.431(2) .
C21 O22 1.456(2) .
N23 C24 1.349(2) .
C24 N28 1.282(2) .
C24 O25 1.357(2) .
O25 C26 1.461(2) .
C26 C29 1.498(3) .
C26 C27 1.535(3) .
C27 N28 1.467(2) .
C29 O30 1.425(2) .
O30 C31 1.377(2) .
C31 C36 1.382(3) .
C31 C32 1.386(3) .
C32 C33 1.384(3) .
C33 C34 1.386(4) .
C34 C35 1.368(4) .
C35 C36 1.391(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O7 C1 C2 C3 -179.0(2) . . . .
C6 C1 C2 C3 1.3(4) . . . .
C1 C2 C3 C4 -0.8(4) . . . .
C2 C3 C4 C5 -0.1(4) . . . .
C3 C4 C5 C6 0.5(4) . . . .
C4 C5 C6 C1 -0.1(4) . . . .
O7 C1 C6 C5 179.4(2) . . . .
C2 C1 C6 C5 -0.8(4) . . . .
C2 C1 O7 C8 14.1(4) . . . .
C6 C1 O7 C8 -166.1(2) . . . .
C1 O7 C8 C9 -122.1(2) . . . .
O7 C8 C9 O10 172.9(2) . . . .
O7 C8 C9 C11 -67.6(3) . . . .
O7 C8 C9 O10' 53.5(4) . . . .
O10 C9 C11 N12 -67.2(2) . . . .
C8 C9 C11 N12 175.64(18) . . . .
O10' C9 C11 N12 50.9(3) . . . .
C9 C11 N12 C13 -94.7(2) . . . .
C9 C11 N12 C17 71.2(2) . . . .
C17 N12 C13 O18 -172.22(18) . . . .
C11 N12 C13 O18 -7.0(3) . . . .
C17 N12 C13 N14 12.4(3) . . . .
C11 N12 C13 N14 177.61(16) . . . .
O18 C13 N14 C15 171.10(17) . . . .
N12 C13 N14 C15 -13.4(3) . . . .
O18 C13 N14 C19 24.1(3) . . . .
N12 C13 N14 C19 -160.44(16) . . . .
C13 N14 C15 O22 -86.40(19) . . . .
C19 N14 C15 O22 62.96(18) . . . .
C13 N14 C15 C16 35.0(2) . . . .
C19 N14 C15 C16 -175.63(15) . . . .
O22 C15 C16 C17 68.19(19) . . . .
N14 C15 C16 C17 -53.9(2) . . . .
C13 N12 C17 C16 -33.3(2) . . . .
C11 N12 C17 C16 161.35(16) . . . .
C15 C16 C17 N12 53.3(2) . . . .
C13 N14 C19 C20 95.11(19) . . . .
C15 N14 C19 C20 -55.4(2) . . . .
N14 C19 C20 C21 50.4(2) . . . .
C19 C20 C21 N23 -171.17(14) . . . .
C19 C20 C21 O22 -51.55(18) . . . .
N14 C15 O22 C21 -63.46(17) . . . .
C16 C15 O22 C21 175.19(14) . . . .
N23 C21 O22 C15 177.30(13) . . . .
C20 C21 O22 C15 57.30(17) . . . .
O22 C21 N23 C24 81.80(19) . . . .
C20 C21 N23 C24 -157.72(16) . . . .
C21 N23 C24 N28 -170.22(17) . . . .
C21 N23 C24 O25 11.0(2) . . . .
N28 C24 O25 C26 -3.2(2) . . . .
N23 C24 O25 C26 175.66(15) . . . .
C24 O25 C26 C29 -119.23(16) . . . .
C24 O25 C26 C27 1.8(2) . . . .
O25 C26 C27 N28 -0.3(2) . . . .
C29 C26 C27 N28 117.88(19) . . . .
N23 C24 N28 C27 -175.76(18) . . . .
O25 C24 N28 C27 3.0(2) . . . .
C26 C27 N28 C24 -1.4(2) . . . .
O25 C26 C29 O30 -67.22(19) . . . .
C27 C26 C29 O30 177.48(16) . . . .
C26 C29 O30 C31 -175.47(16) . . . .
C29 O30 C31 C36 -2.5(3) . . . .
C29 O30 C31 C32 177.78(18) . . . .
O30 C31 C32 C33 179.64(19) . . . .
C36 C31 C32 C33 -0.1(3) . . . .
C31 C32 C33 C34 -0.7(4) . . . .
C32 C33 C34 C35 0.9(4) . . . .
C33 C34 C35 C36 -0.4(4) . . . .
O30 C31 C36 C35 -179.1(2) . . . .
C32 C31 C36 C35 0.6(4) . . . .
C34 C35 C36 C31 -0.4(4) . . . .
