#------------------------------------------------------------------------------
#$Date: 2020-10-24 02:12:28 +0300 (Sat, 24 Oct 2020) $
#$Revision: 258587 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038922.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_4038922
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            'C44 H29 N3'
_chemical_formula_weight         599.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                102.3551(18)
_cell_angle_beta                 103.2875(18)
_cell_angle_gamma                104.9579(18)
_cell_formula_units_Z            2
_cell_length_a                   11.7391(6)
_cell_length_b                   12.2007(7)
_cell_length_c                   13.0911(7)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.69
_cell_volume                     1686.84(16)
_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 0.994
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            46030
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.694
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.215
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         7737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0603
_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)+(0.0528P)²+1.0867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6089
_reflns_number_total             7737
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01882_si_003.cif
_cod_data_source_block           P3g
_cod_database_code               4038922
_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. 
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.19755(15) -0.11652(15) 0.57728(13) 0.0265(3) Uani 1 1 d . . . . .
C2 C 0.30735(15) 0.05658(15) 0.55653(13) 0.0271(3) Uani 1 1 d . . . . .
C3 C 0.21257(16) 0.04017(16) 0.46342(14) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.218911 0.095583 0.422197 0.035 Uiso 1 1 calc R U . . .
C4 C 0.10802(15) -0.05924(15) 0.43176(13) 0.0275(4) Uani 1 1 d . . . . .
C5 C 0.18707(15) -0.20413(16) 0.64038(14) 0.0282(4) Uani 1 1 d . . . . .
C6 C 0.26689(16) -0.17782(17) 0.74556(15) 0.0323(4) Uani 1 1 d . . . . .
H6 H 0.330611 -0.103328 0.777004 0.039 Uiso 1 1 calc R U . . .
C7 C 0.25412(18) -0.25935(19) 0.80464(16) 0.0391(4) Uani 1 1 d . . . . .
H7 H 0.308523 -0.240143 0.876628 0.047 Uiso 1 1 calc R U . . .
C8 C 0.16274(18) -0.36844(19) 0.75952(18) 0.0418(5) Uani 1 1 d . . . . .
H8 H 0.154856 -0.424717 0.799790 0.050 Uiso 1 1 calc R U . . .
C9 C 0.08304(18) -0.39511(19) 0.65562(18) 0.0423(5) Uani 1 1 d . . . . .
H9 H 0.020074 -0.470097 0.624435 0.051 Uiso 1 1 calc R U . . .
C10 C 0.09382(17) -0.31370(17) 0.59623(16) 0.0359(4) Uani 1 1 d . . . . .
H10 H 0.037475 -0.332602 0.525175 0.043 Uiso 1 1 calc R U . . .
C19 C 0.42295(15) 0.15873(15) 0.59117(13) 0.0272(4) Uani 1 1 d . . . . .
C20 C 0.53492(16) 0.13573(17) 0.60715(14) 0.0309(4) Uani 1 1 d . . . . .
H20 H 0.535671 0.057312 0.603434 0.037 Uiso 1 1 calc R U . . .
C21 C 0.64461(16) 0.22458(17) 0.62825(14) 0.0334(4) Uani 1 1 d . . . . .
H21 H 0.719433 0.206131 0.636632 0.040 Uiso 1 1 calc R U . . .
C22 C 0.64724(16) 0.34107(17) 0.63745(14) 0.0319(4) Uani 1 1 d . . . . .
C27 C 0.53500(15) 0.36798(15) 0.62607(13) 0.0273(4) Uani 1 1 d . . . . .
C28 C 0.42149(15) 0.27567(15) 0.60239(13) 0.0264(3) Uani 1 1 d . . . . .
C29 C 0.31049(16) 0.30778(17) 0.59388(14) 0.0309(4) Uani 1 1 d . . . . .
H29 H 0.234196 0.248041 0.580944 0.037 Uiso 1 1 calc R U . . .
C30 C 0.31247(17) 0.42058(17) 0.60385(14) 0.0340(4) Uani 1 1 d . . . . .
H30 H 0.237346 0.438247 0.597091 0.041 Uiso 1 1 calc R U . . .
C31 C 0.42489(18) 0.51449(16) 0.62438(14) 0.0336(4) Uani 1 1 d . . . . .
C32 C 0.4279(2) 0.63146(18) 0.63364(16) 0.0419(5) Uani 1 1 d . . . . .
H32 H 0.353220 0.650186 0.624212 0.050 Uiso 1 1 calc R U . . .
C33 C 0.5385(2) 0.71997(18) 0.65636(16) 0.0479(5) Uani 1 1 d . . . . .
H33 H 0.539244 0.799177 0.662422 0.057 Uiso 1 1 calc R U . . .
C34 C 0.6478(2) 0.69465(18) 0.67034(16) 0.0457(5) Uani 1 1 d . . . . .
H34 H 0.723205 0.757078 0.687151 0.055 Uiso 1 1 calc R U . . .
C25 C 0.64996(18) 0.57940(17) 0.66032(14) 0.0369(4) Uani 1 1 d . . . . .
C26 C 0.53617(17) 0.48684(16) 0.63711(13) 0.0306(4) Uani 1 1 d . . . . .
C24 C 0.76084(19) 0.5481(2) 0.66997(17) 0.0446(5) Uani 1 1 d . . . . .
H24 H 0.837179 0.608483 0.684609 0.054 Uiso 1 1 calc R U . . .
C23 C 0.75974(17) 0.43606(19) 0.65892(16) 0.0406(5) Uani 1 1 d . . . . .
H23 H 0.835153 0.418976 0.665429 0.049 Uiso 1 1 calc R U . . .
C11 C 0.00259(15) -0.08311(16) 0.33414(13) 0.0277(4) Uani 1 1 d . . . . .
C12 C -0.01792(16) 0.00679(16) 0.29011(14) 0.0313(4) Uani 1 1 d . . . . .
H12 H 0.035691 0.085953 0.324912 0.038 Uiso 1 1 calc R U . . .
C13 C -0.11468(16) -0.01678(17) 0.19681(14) 0.0322(4) Uani 1 1 d . . . . .
H13 H -0.126112 0.046094 0.167983 0.039 Uiso 1 1 calc R U . . .
C14 C -0.19551(15) -0.13144(17) 0.14461(14) 0.0302(4) Uani 1 1 d . . . . .
C15 C -0.17671(17) -0.22168(17) 0.18954(15) 0.0346(4) Uani 1 1 d . . . . .
H15 H -0.231494 -0.300529 0.155762 0.041 Uiso 1 1 calc R U . . .
C16 C -0.07953(16) -0.19768(16) 0.28239(14) 0.0317(4) Uani 1 1 d . . . . .
H16 H -0.068392 -0.260397 0.311585 0.038 Uiso 1 1 calc R U . . .
C17 C -0.40692(15) -0.24915(17) 0.03129(14) 0.0303(4) Uani 1 1 d . . . . .
C35 C -0.46371(17) -0.24999(19) 0.11322(15) 0.0376(4) Uani 1 1 d . . . . .
H35 H -0.427131 -0.190125 0.181706 0.045 Uiso 1 1 calc R U . . .
C36 C -0.57346(18) -0.3380(2) 0.09500(16) 0.0429(5) Uani 1 1 d . . . . .
H36 H -0.612101 -0.338876 0.151247 0.051 Uiso 1 1 calc R U . . .
C37 C -0.62745(18) -0.42495(19) -0.00489(16) 0.0405(5) Uani 1 1 d . . . . .
H37 H -0.703377 -0.485024 -0.017462 0.049 Uiso 1 1 calc R U . . .
C38 C -0.57059(17) -0.42413(17) -0.08627(15) 0.0360(4) Uani 1 1 d . . . . .
H38 H -0.607438 -0.483998 -0.154738 0.043 Uiso 1 1 calc R U . . .
C39 C -0.46033(16) -0.33662(17) -0.06859(14) 0.0322(4) Uani 1 1 d . . . . .
H39 H -0.421332 -0.336441 -0.124637 0.039 Uiso 1 1 calc R U . . .
C18 C -0.28891(16) -0.08698(16) -0.02367(14) 0.0300(4) Uani 1 1 d . . . . .
C40 C -0.18258(18) -0.04950(19) -0.05342(16) 0.0393(4) Uani 1 1 d . . . . .
H40 H -0.112134 -0.070498 -0.024082 0.047 Uiso 1 1 calc R U . . .
C41 C -0.1786(2) 0.0180(2) -0.12524(18) 0.0507(6) Uani 1 1 d . . . . .
H41 H -0.104719 0.044741 -0.143800 0.061 Uiso 1 1 calc R U . . .
C42 C -0.2806(2) 0.0469(2) -0.1703(2) 0.0581(7) Uani 1 1 d . . . . .
H42 H -0.277766 0.092544 -0.220613 0.070 Uiso 1 1 calc R U . . .
C43 C -0.3864(2) 0.0093(2) -0.1421(2) 0.0491(5) Uani 1 1 d . . . . .
H43 H -0.457081 0.029167 -0.173118 0.059 Uiso 1 1 calc R U . . .
C44 C -0.39150(17) -0.05706(17) -0.06903(16) 0.0362(4) Uani 1 1 d . . . . .
H44 H -0.465210 -0.082268 -0.049806 0.043 Uiso 1 1 calc R U . . .
N1 N 0.30111(13) -0.02215(13) 0.61452(11) 0.0277(3) Uani 1 1 d . . . . .
N2 N 0.10117(12) -0.13860(13) 0.48888(11) 0.0277(3) Uani 1 1 d . . . . .
N3 N -0.29408(13) -0.15734(15) 0.04944(12) 0.0356(4) 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'
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 126.24(15) . . ?
N2 C1 C5 116.42(15) . . ?
N1 C1 C5 117.34(14) . . ?
N1 C2 C3 121.59(15) . . ?
N1 C2 C19 117.81(14) . . ?
C3 C2 C19 120.49(15) . . ?
C2 C3 C4 118.46(15) . . ?
N2 C4 C3 120.37(15) . . ?
N2 C4 C11 117.64(15) . . ?
C3 C4 C11 121.98(15) . . ?
C6 C5 C10 118.70(16) . . ?
C6 C5 C1 121.13(16) . . ?
C10 C5 C1 120.14(15) . . ?
C7 C6 C5 120.53(18) . . ?
C8 C7 C6 120.36(18) . . ?
C9 C8 C7 119.52(18) . . ?
C8 C9 C10 120.68(19) . . ?
C9 C10 C5 120.20(18) . . ?
C20 C19 C28 119.86(15) . . ?
C20 C19 C2 118.11(16) . . ?
C28 C19 C2 121.95(15) . . ?
C21 C20 C19 121.22(17) . . ?
C20 C21 C22 120.85(17) . . ?
C21 C22 C27 119.13(16) . . ?
C21 C22 C23 122.47(17) . . ?
C27 C22 C23 118.40(18) . . ?
C22 C27 C26 119.93(16) . . ?
C22 C27 C28 119.90(16) . . ?
C26 C27 C28 120.16(16) . . ?
C19 C28 C27 118.95(15) . . ?
C19 C28 C29 123.21(15) . . ?
C27 C28 C29 117.82(16) . . ?
C30 C29 C28 121.53(17) . . ?
C29 C30 C31 121.72(17) . . ?
C32 C31 C26 119.50(18) . . ?
C32 C31 C30 122.26(19) . . ?
C26 C31 C30 118.23(17) . . ?
C33 C32 C31 120.5(2) . . ?
C34 C33 C32 120.6(2) . . ?
C33 C34 C25 121.3(2) . . ?
C34 C25 C26 118.7(2) . . ?
C34 C25 C24 123.24(19) . . ?
C26 C25 C24 118.03(18) . . ?
C31 C26 C27 120.48(16) . . ?
C31 C26 C25 119.34(17) . . ?
C27 C26 C25 120.18(17) . . ?
C23 C24 C25 121.84(18) . . ?
C24 C23 C22 121.60(19) . . ?
C12 C11 C16 117.77(15) . . ?
C12 C11 C4 121.63(16) . . ?
C16 C11 C4 120.60(16) . . ?
C13 C12 C11 121.31(17) . . ?
C12 C13 C14 120.75(17) . . ?
C13 C14 C15 118.20(16) . . ?
C13 C14 N3 121.63(16) . . ?
C15 C14 N3 120.17(16) . . ?
C16 C15 C14 120.78(17) . . ?
C15 C16 C11 121.19(17) . . ?
C39 C17 C35 120.03(17) . . ?
C39 C17 N3 120.01(16) . . ?
C35 C17 N3 119.96(16) . . ?
C36 C35 C17 119.84(18) . . ?
C35 C36 C37 120.26(18) . . ?
C38 C37 C36 119.80(18) . . ?
C37 C38 C39 120.34(18) . . ?
C38 C39 C17 119.72(17) . . ?
C40 C18 C44 118.86(17) . . ?
C40 C18 N3 120.67(16) . . ?
C44 C18 N3 120.45(16) . . ?
C41 C40 C18 120.35(18) . . ?
C42 C41 C40 120.6(2) . . ?
C43 C42 C41 119.5(2) . . ?
C42 C43 C44 120.74(19) . . ?
C43 C44 C18 120.02(18) . . ?
C2 N1 C1 116.03(14) . . ?
C1 N2 C4 117.30(14) . . ?
C14 N3 C18 121.49(15) . . ?
C14 N3 C17 119.34(14) . . ?
C18 N3 C17 118.87(14) . . ?
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 1.341(2) . ?
C1 N1 1.344(2) . ?
C1 C5 1.482(2) . ?
C2 N1 1.344(2) . ?
C2 C3 1.386(2) . ?
C2 C19 1.484(2) . ?
C3 C4 1.390(2) . ?
C4 N2 1.342(2) . ?
C4 C11 1.476(2) . ?
C5 C6 1.393(2) . ?
C5 C10 1.394(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.385(3) . ?
C19 C20 1.393(2) . ?
C19 C28 1.408(2) . ?
C20 C21 1.377(2) . ?
C21 C22 1.392(3) . ?
C22 C27 1.421(2) . ?
C22 C23 1.437(2) . ?
C27 C26 1.422(3) . ?
C27 C28 1.423(2) . ?
C28 C29 1.442(2) . ?
C29 C30 1.348(3) . ?
C30 C31 1.432(3) . ?
C31 C32 1.396(3) . ?
C31 C26 1.414(3) . ?
C32 C33 1.378(3) . ?
C33 C34 1.377(3) . ?
C34 C25 1.391(3) . ?
C25 C26 1.428(3) . ?
C25 C24 1.434(3) . ?
C24 C23 1.340(3) . ?
C11 C12 1.392(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.381(2) . ?
C13 C14 1.390(3) . ?
C14 C15 1.396(3) . ?
C14 N3 1.404(2) . ?
C15 C16 1.379(2) . ?
C17 C39 1.386(3) . ?
C17 C35 1.387(3) . ?
C17 N3 1.429(2) . ?
C35 C36 1.380(3) . ?
C36 C37 1.384(3) . ?
C37 C38 1.381(3) . ?
C38 C39 1.383(3) . ?
C18 C40 1.387(3) . ?
C18 C44 1.388(2) . ?
C18 N3 1.417(2) . ?
C40 C41 1.377(3) . ?
C41 C42 1.374(3) . ?
C42 C43 1.371(3) . ?
C43 C44 1.381(3) . ?
