#------------------------------------------------------------------------------
#$Date: 2020-10-10 02:38:19 +0300 (Sat, 10 Oct 2020) $
#$Revision: 258278 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038879.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_4038879
loop_
_publ_author_name
'El-Hage, Firas'
'Schöll, Christopher'
'Pospech, Jola'
_publ_section_title
;
 Photo-mediated Decarboxylative Giese-Type Reaction using Organic
 Pyrimidopteridine Photoredox Catalysts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01955
_journal_year                    2020
_chemical_formula_sum            'C16 H24 O4'
_chemical_formula_weight         280.35
_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_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.5215(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3426(9)
_cell_length_b                   21.642(2)
_cell_length_c                   7.3217(7)
_cell_measurement_reflns_used    8424
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.19
_cell_volume                     1473.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         1.882
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0410
_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)+(0.0555P)²+0.5196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2926
_reflns_number_total             3562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01955_si_001.cif
_cod_data_source_block           AX1922
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038879
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_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_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 0.20323(13) 0.34870(6) 1.20500(17) 0.0281(3) Uani 1 1 d . . . . .
C2 C 0.31301(14) 0.33515(5) 1.07161(17) 0.0271(3) Uani 1 1 d . . . . .
H2A H 0.272444 0.304697 0.979866 0.032 Uiso 1 1 calc R U . . .
H2B H 0.399358 0.316506 1.138949 0.032 Uiso 1 1 calc R U . . .
C3 C 0.35711(12) 0.39339(5) 0.97223(15) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.394132 0.424075 1.067422 0.025 Uiso 1 1 calc R U . . .
C4 C 0.47808(12) 0.38194(5) 0.84272(15) 0.0196(2) Uani 1 1 d . . . . .
C5 C 0.51203(14) 0.44235(5) 0.74404(18) 0.0273(3) Uani 1 1 d . . . . .
H5A H 0.425110 0.456454 0.667352 0.033 Uiso 1 1 calc R U . . .
H5B H 0.539061 0.474812 0.836243 0.033 Uiso 1 1 calc R U . . .
C6 C 0.63546(14) 0.43293(6) 0.62249(18) 0.0309(3) Uani 1 1 d . . . . .
H6 H 0.655117 0.472686 0.559926 0.037 Uiso 1 1 calc R U . . .
C7 C 0.77086(14) 0.41217(6) 0.73986(18) 0.0317(3) Uani 1 1 d . . . . .
H7A H 0.800415 0.444252 0.832258 0.038 Uiso 1 1 calc R U . . .
H7B H 0.850343 0.406106 0.661465 0.038 Uiso 1 1 calc R U . . .
C8 C 0.73969(13) 0.35146(6) 0.83620(17) 0.0285(3) Uani 1 1 d . . . . .
H8 H 0.827922 0.337680 0.913642 0.034 Uiso 1 1 calc R U . . .
C9 C 0.69533(14) 0.30182(6) 0.69252(18) 0.0317(3) Uani 1 1 d . . . . .
H9A H 0.774289 0.294846 0.613897 0.038 Uiso 1 1 calc R U . . .
H9B H 0.676064 0.262429 0.754382 0.038 Uiso 1 1 calc R U . . .
C10 C 0.56021(14) 0.32292(6) 0.57475(17) 0.0311(3) Uani 1 1 d . . . . .
H10 H 0.531917 0.290655 0.480357 0.037 Uiso 1 1 calc R U . . .
C11 C 0.43688(13) 0.33233(6) 0.69648(16) 0.0267(3) Uani 1 1 d . . . . .
H11A H 0.416181 0.292887 0.757173 0.032 Uiso 1 1 calc R U . . .
H11B H 0.348953 0.345271 0.619738 0.032 Uiso 1 1 calc R U . . .
C12 C 0.61667(13) 0.36150(6) 0.95831(16) 0.0250(2) Uani 1 1 d . . . . .
H12A H 0.645120 0.393477 1.051481 0.030 Uiso 1 1 calc R U . . .
H12B H 0.598356 0.322617 1.023396 0.030 Uiso 1 1 calc R U . . .
C13 C 0.59143(15) 0.38375(7) 0.47834(17) 0.0350(3) Uani 1 1 d . . . . .
H13A H 0.669785 0.377490 0.398303 0.042 Uiso 1 1 calc R U . . .
H13B H 0.504581 0.397443 0.400781 0.042 Uiso 1 1 calc R U . . .
C14 C 0.03939(16) 0.30293(8) 1.3920(2) 0.0413(3) Uani 1 1 d . . . . .
H14A H 0.077305 0.326467 1.500389 0.062 Uiso 1 1 calc R U . . .
H14B H 0.008463 0.262012 1.430028 0.062 Uiso 1 1 calc R U . . .
H14C H -0.042804 0.324936 1.329172 0.062 Uiso 1 1 calc R U . . .
C15 C 0.22383(12) 0.42068(5) 0.86728(16) 0.0246(2) Uani 1 1 d . . . . .
C16 C 0.10735(15) 0.51266(7) 0.7619(2) 0.0450(4) Uani 1 1 d . . . . .
H16A H 0.102496 0.498788 0.634041 0.067 Uiso 1 1 calc R U . . .
H16B H 0.121199 0.557533 0.766949 0.067 Uiso 1 1 calc R U . . .
H16C H 0.017562 0.502006 0.813474 0.067 Uiso 1 1 calc R U . . .
O1 O 0.15076(11) 0.29606(4) 1.26839(13) 0.0357(2) Uani 1 1 d . . . . .
O2 O 0.16809(13) 0.39918(5) 1.25202(16) 0.0472(3) Uani 1 1 d . . . . .
O3 O 0.12725(10) 0.39060(5) 0.79091(16) 0.0416(3) Uani 1 1 d . . . . .
O4 O 0.22650(9) 0.48264(4) 0.86696(13) 0.0317(2) 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'
O O 0.0106 0.0060 '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
O2 C1 O1 123.69(12) . . ?
O2 C1 C2 125.67(12) . . ?
O1 C1 C2 110.63(10) . . ?
C1 C2 C3 112.18(10) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C15 C3 C2 108.39(9) . . ?
C15 C3 C4 111.11(9) . . ?
C2 C3 C4 113.64(9) . . ?
C15 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C4 C3 H3 107.8 . . ?
C11 C4 C5 108.34(9) . . ?
C11 C4 C12 108.80(9) . . ?
C5 C4 C12 107.51(9) . . ?
C11 C4 C3 112.68(9) . . ?
C5 C4 C3 110.08(9) . . ?
C12 C4 C3 109.30(9) . . ?
C6 C5 C4 111.02(9) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C13 109.71(11) . . ?
C7 C6 C5 109.90(10) . . ?
C13 C6 C5 109.00(11) . . ?
C7 C6 H6 109.4 . . ?
C13 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C6 C7 C8 109.12(10) . . ?
C6 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 C9 109.62(10) . . ?
C7 C8 C12 109.41(10) . . ?
C9 C8 C12 109.28(10) . . ?
C7 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C12 C8 H8 109.5 . . ?
C10 C9 C8 109.39(10) . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C9 C10 C13 109.42(11) . . ?
C9 C10 C11 109.70(10) . . ?
C13 C10 C11 109.84(11) . . ?
C9 C10 H10 109.3 . . ?
C13 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C10 C11 C4 110.17(10) . . ?
C10 C11 H11A 109.6 . . ?
C4 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C4 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C8 C12 C4 110.89(9) . . ?
C8 C12 H12A 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C6 C13 C10 109.29(10) . . ?
C6 C13 H13A 109.8 . . ?
C10 C13 H13A 109.8 . . ?
C6 C13 H13B 109.8 . . ?
C10 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 123.53(11) . . ?
O3 C15 C3 124.42(11) . . ?
O4 C15 C3 112.04(10) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 O1 C14 115.91(11) . . ?
C15 O4 C16 115.91(10) . . ?
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 O2 1.2006(16) . ?
C1 O1 1.3406(15) . ?
C1 C2 1.5114(17) . ?
C2 C3 1.5316(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C15 1.5184(15) . ?
C3 C4 1.5633(15) . ?
C3 H3 1.0000 . ?
C4 C11 1.5389(15) . ?
C4 C5 1.5414(15) . ?
C4 C12 1.5420(15) . ?
C5 C6 1.5366(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5269(18) . ?
C6 C13 1.527(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.5323(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5324(18) . ?
C8 C12 1.5379(17) . ?
C8 H8 1.0000 . ?
C9 C10 1.5285(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.5348(19) . ?
C10 C11 1.5366(17) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O1 1.4510(16) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O3 1.2057(15) . ?
C15 O4 1.3412(14) . ?
C16 O4 1.4450(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
_geom_torsion_publ_flag
O2 C1 C2 C3 -10.64(19) . . . . ?
O1 C1 C2 C3 170.55(10) . . . . ?
C1 C2 C3 C15 -59.80(13) . . . . ?
C1 C2 C3 C4 176.15(10) . . . . ?
C15 C3 C4 C11 -65.45(12) . . . . ?
C2 C3 C4 C11 57.11(13) . . . . ?
C15 C3 C4 C5 55.60(12) . . . . ?
C2 C3 C4 C5 178.16(10) . . . . ?
C15 C3 C4 C12 173.46(9) . . . . ?
C2 C3 C4 C12 -63.98(12) . . . . ?
C11 C4 C5 C6 -58.94(13) . . . . ?
C12 C4 C5 C6 58.48(13) . . . . ?
C3 C4 C5 C6 177.44(9) . . . . ?
C4 C5 C6 C7 -60.01(13) . . . . ?
C4 C5 C6 C13 60.26(13) . . . . ?
C13 C6 C7 C8 -60.32(13) . . . . ?
C5 C6 C7 C8 59.51(13) . . . . ?
C6 C7 C8 C9 60.02(13) . . . . ?
C6 C7 C8 C12 -59.80(13) . . . . ?
C7 C8 C9 C10 -60.01(13) . . . . ?
C12 C8 C9 C10 59.89(13) . . . . ?
C8 C9 C10 C13 59.86(13) . . . . ?
C8 C9 C10 C11 -60.70(13) . . . . ?
C9 C10 C11 C4 60.29(13) . . . . ?
C13 C10 C11 C4 -60.02(13) . . . . ?
C5 C4 C11 C10 58.35(13) . . . . ?
C12 C4 C11 C10 -58.24(12) . . . . ?
C3 C4 C11 C10 -179.61(9) . . . . ?
C7 C8 C12 C4 60.76(13) . . . . ?
C9 C8 C12 C4 -59.27(13) . . . . ?
C11 C4 C12 C8 58.12(12) . . . . ?
C5 C4 C12 C8 -59.00(12) . . . . ?
C3 C4 C12 C8 -178.46(9) . . . . ?
C7 C6 C13 C10 60.40(13) . . . . ?
C5 C6 C13 C10 -59.97(13) . . . . ?
C9 C10 C13 C6 -60.05(14) . . . . ?
C11 C10 C13 C6 60.42(14) . . . . ?
C2 C3 C15 O3 -36.89(16) . . . . ?
C4 C3 C15 O3 88.66(14) . . . . ?
C2 C3 C15 O4 143.95(10) . . . . ?
C4 C3 C15 O4 -90.50(11) . . . . ?
O2 C1 O1 C14 3.7(2) . . . . ?
C2 C1 O1 C14 -177.42(11) . . . . ?
O3 C15 O4 C16 -2.33(19) . . . . ?
C3 C15 O4 C16 176.84(11) . . . . ?
