#------------------------------------------------------------------------------
#$Date: 2020-10-24 02:12:03 +0300 (Sat, 24 Oct 2020) $
#$Revision: 258586 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038921.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_4038921
loop_
_publ_author_name
'Mondal, Rajarshi'
'Lozada, Issiah B.'
'Stotska, Olha'
'Herbert, David E.'
_publ_section_title
;
 Catalytic Synthesis of Luminescent Pyrimidines via Acceptor-less
 Dehydrogenative Coupling
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01882
_journal_year                    2020
_chemical_formula_sum            'C29 H25 N3 O'
_chemical_formula_weight         431.52
_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-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 92.646(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5603(5)
_cell_length_b                   15.4396(7)
_cell_length_c                   14.7968(7)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.04
_cell_measurement_theta_min      2.91
_cell_volume                     2181.79(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            76282
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.222
_diffrn_reflns_theta_min         2.508
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         8105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0661
_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/[σ²(Fo²)+(0.0716P)²+1.3872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1665
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6043
_reflns_number_total             8105
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01882_si_002.cif
_cod_data_source_block           P1c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038921
_shelx_shelxl_version_number     2017/1
_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 0.31525(14) 0.37632(8) 0.68605(9) 0.0199(2) Uani 1 1 d . . . . .
C2 C 0.39403(14) 0.23894(8) 0.66295(9) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.31960(14) 0.21082(9) 0.73613(9) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.322849 0.151902 0.754600 0.027 Uiso 1 1 calc R U . . .
C4 C 0.24024(14) 0.27103(8) 0.78167(9) 0.0205(2) Uani 1 1 d . . . . .
C5 C 0.31451(14) 0.46919(8) 0.65992(9) 0.0207(2) Uani 1 1 d . . . . .
C6 C 0.42071(15) 0.50318(9) 0.60876(10) 0.0250(3) Uani 1 1 d . . . . .
H6 H 0.495431 0.467041 0.591650 0.030 Uiso 1 1 calc R U . . .
C7 C 0.41749(17) 0.58986(9) 0.58273(10) 0.0280(3) Uani 1 1 d . . . . .
H7 H 0.490520 0.612871 0.548523 0.034 Uiso 1 1 calc R U . . .
C8 C 0.30776(17) 0.64265(9) 0.60670(10) 0.0272(3) Uani 1 1 d . . . . .
H8 H 0.304518 0.701425 0.587735 0.033 Uiso 1 1 calc R U . . .
C9 C 0.20275(16) 0.60952(9) 0.65839(10) 0.0257(3) Uani 1 1 d . . . . .
H9 H 0.128154 0.645841 0.675341 0.031 Uiso 1 1 calc R U . . .
C10 C 0.20649(14) 0.52353(9) 0.68535(9) 0.0221(3) Uani 1 1 d . . . . .
H10 H 0.134971 0.501425 0.721416 0.027 Uiso 1 1 calc R U . . .
C11 C 0.15693(14) 0.24739(9) 0.85916(9) 0.0213(2) Uani 1 1 d . . . . .
C12 C 0.17695(15) 0.16881(10) 0.90514(10) 0.0255(3) Uani 1 1 d . . . . .
H12 H 0.244551 0.129047 0.884869 0.031 Uiso 1 1 calc R U . . .
C13 C 0.10117(15) 0.14755(10) 0.97909(10) 0.0275(3) Uani 1 1 d . . . . .
H13 H 0.118869 0.094047 1.009203 0.033 Uiso 1 1 calc R U . . .
C14 C -0.00183(15) 0.20355(10) 1.01078(9) 0.0242(3) Uani 1 1 d . . . . .
C15 C -0.02275(15) 0.28239(9) 0.96431(10) 0.0257(3) Uani 1 1 d . . . . .
H15 H -0.091812 0.321698 0.983531 0.031 Uiso 1 1 calc R U . . .
C16 C 0.05564(15) 0.30367(9) 0.89103(10) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.040224 0.357807 0.861722 0.030 Uiso 1 1 calc R U . . .
C17 C -0.17723(19) 0.24082(12) 1.12073(12) 0.0375(4) Uani 1 1 d . . . . .
H17A H -0.143041 0.300344 1.115288 0.056 Uiso 1 1 calc R U . . .
H17B H -0.189340 0.227328 1.184616 0.056 Uiso 1 1 calc R U . . .
H17C H -0.267266 0.234933 1.086873 0.056 Uiso 1 1 calc R U . . .
C18 C -0.0975(2) 0.09246(13) 1.10976(15) 0.0491(5) Uani 1 1 d . . . . .
H18A H -0.190922 0.073432 1.088153 0.074 Uiso 1 1 calc R U . . .
H18B H -0.088801 0.087017 1.175770 0.074 Uiso 1 1 calc R U . . .
H18C H -0.026463 0.056319 1.082485 0.074 Uiso 1 1 calc R U . . .
C19 C 0.47552(14) 0.17793(8) 0.60886(9) 0.0198(2) Uani 1 1 d . . . . .
C20 C 0.54902(14) 0.10829(9) 0.65129(9) 0.0218(2) Uani 1 1 d . . . . .
H20 H 0.541191 0.098741 0.714277 0.026 Uiso 1 1 calc R U . . .
C21 C 0.63137(14) 0.05441(9) 0.60273(9) 0.0215(2) Uani 1 1 d . . . . .
H21 H 0.680793 0.008472 0.632605 0.026 Uiso 1 1 calc R U . . .
C22 C 0.64360(14) 0.06650(8) 0.50846(9) 0.0194(2) Uani 1 1 d . . . . .
C23 C 0.73343(14) 0.01383(8) 0.45778(9) 0.0213(2) Uani 1 1 d . . . . .
H23 H 0.787809 -0.030422 0.486933 0.026 Uiso 1 1 calc R U . . .
C24 C 0.74111(15) 0.02731(9) 0.36657(9) 0.0232(3) Uani 1 1 d . . . . .
C25 C 0.65784(16) 0.09129(9) 0.32184(9) 0.0248(3) Uani 1 1 d . . . . .
H25 H 0.661523 0.098297 0.258212 0.030 Uiso 1 1 calc R U . . .
C26 C 0.57221(15) 0.14304(9) 0.36964(9) 0.0227(3) Uani 1 1 d . . . . .
H26 H 0.517344 0.186132 0.338919 0.027 Uiso 1 1 calc R U . . .
C27 C 0.56402(14) 0.13333(8) 0.46470(9) 0.0192(2) Uani 1 1 d . . . . .
C28 C 0.48173(14) 0.18889(8) 0.51657(9) 0.0203(2) Uani 1 1 d . . . . .
H28 H 0.430036 0.234358 0.487499 0.024 Uiso 1 1 calc R U . . .
C29 C 0.92166(18) -0.07730(11) 0.35330(12) 0.0342(3) Uani 1 1 d . . . . .
H29A H 0.985188 -0.045960 0.395642 0.051 Uiso 1 1 calc R U . . .
H29B H 0.975971 -0.105550 0.307074 0.051 Uiso 1 1 calc R U . . .
H29C H 0.870278 -0.121186 0.386248 0.051 Uiso 1 1 calc R U . . .
N1 N 0.39360(12) 0.32281(7) 0.63781(8) 0.0213(2) Uani 1 1 d . . . . .
N2 N 0.23816(12) 0.35474(7) 0.75596(8) 0.0216(2) Uani 1 1 d . . . . .
N3 N -0.07718(16) 0.18171(10) 1.08455(10) 0.0366(3) Uani 1 1 d . . . . .
O1 O 0.82517(12) -0.01804(7) 0.31107(7) 0.0307(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'
N N 0.0061 0.0033 '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
N2 C1 N1 126.72(12) . . ?
N2 C1 C5 116.42(11) . . ?
N1 C1 C5 116.86(11) . . ?
N1 C2 C3 121.28(12) . . ?
N1 C2 C19 117.20(11) . . ?
C3 C2 C19 121.51(12) . . ?
C2 C3 C4 118.52(12) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
N2 C4 C3 120.32(12) . . ?
N2 C4 C11 117.16(11) . . ?
C3 C4 C11 122.52(12) . . ?
C10 C5 C6 119.05(12) . . ?
C10 C5 C1 120.33(12) . . ?
C6 C5 C1 120.61(12) . . ?
C7 C6 C5 120.25(13) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.08(13) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.95(13) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.13(13) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 120.52(13) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C16 C11 C12 117.11(12) . . ?
C16 C11 C4 121.09(12) . . ?
C12 C11 C4 121.79(12) . . ?
C13 C12 C11 121.79(13) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 121.28(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
N3 C14 C13 120.89(13) . . ?
N3 C14 C15 122.08(13) . . ?
C13 C14 C15 117.03(12) . . ?
C16 C15 C14 121.16(13) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C11 121.62(13) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 C19 C20 119.27(12) . . ?
C28 C19 C2 120.31(12) . . ?
C20 C19 C2 120.42(12) . . ?
C21 C20 C19 120.91(12) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 120.75(12) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C27 118.52(12) . . ?
C21 C22 C23 121.54(12) . . ?
C27 C22 C23 119.94(12) . . ?
C24 C23 C22 119.58(12) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
O1 C24 C23 124.96(13) . . ?
O1 C24 C25 114.22(12) . . ?
C23 C24 C25 120.82(12) . . ?
C26 C25 C24 120.32(13) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.89(13) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C28 C27 C26 122.07(12) . . ?
C28 C27 C22 119.54(12) . . ?
C26 C27 C22 118.38(12) . . ?
C19 C28 C27 120.87(12) . . ?
C19 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
O1 C29 H29A 109.5 . . ?
O1 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O1 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C1 N1 C2 116.06(11) . . ?
C1 N2 C4 117.08(11) . . ?
C14 N3 C17 121.28(14) . . ?
C14 N3 C18 121.34(14) . . ?
C17 N3 C18 114.13(13) . . ?
C24 O1 C29 116.89(12) . . ?
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 N2 1.3396(16) . ?
C1 N1 1.3426(17) . ?
C1 C5 1.4850(18) . ?
C2 N1 1.3473(17) . ?
C2 C3 1.3923(18) . ?
C2 C19 1.4807(18) . ?
C3 C4 1.3932(18) . ?
C3 H3 0.9500 . ?
C4 N2 1.3471(17) . ?
C4 C11 1.4719(18) . ?
C5 C10 1.3957(19) . ?
C5 C6 1.3966(18) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3862(19) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.3991(19) . ?
C11 C12 1.3998(19) . ?
C12 C13 1.3796(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.407(2) . ?
C13 H13 0.9500 . ?
C14 N3 1.3773(18) . ?
C14 C15 1.408(2) . ?
C15 C16 1.3857(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N3 1.443(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N3 1.443(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C28 1.3801(18) . ?
C19 C20 1.4153(19) . ?
C20 C21 1.3712(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.4175(18) . ?
C21 H21 0.9500 . ?
C22 C27 1.4203(18) . ?
C22 C23 1.4214(18) . ?
C23 C24 1.3709(19) . ?
C23 H23 0.9500 . ?
C24 O1 1.3680(16) . ?
C24 C25 1.414(2) . ?
C25 C26 1.3645(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.4203(18) . ?
C26 H26 0.9500 . ?
C27 C28 1.4141(18) . ?
C28 H28 0.9500 . ?
C29 O1 1.423(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
