#------------------------------------------------------------------------------
#$Date: 2022-07-06 10:23:37 +0200 (Wed 06 de Jul de 2022) $
#$Revision: 276652 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/14/7061479.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_7061479
loop_
_publ_author_name
'De, Rimpa'
'Sengupta, Utsav'
'Savarimuthu, Antony'
'Misra, Souvik'
'Nanda, Jayanta'
'Bera, Mrinal K.'
_publ_section_title
;
 A practical and cost-effective approach to polysubstituted pyrimidine
 derivatives via DBU mediated redox isomerization of propargyl alcohol and
 subsequent N--C--N fragment condensation
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10603
_journal_page_last               10610
_journal_paper_doi               10.1039/D2NJ00586G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C H N'
_chemical_formula_weight         27.03
_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-2014/7
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                93.56(5)
_cell_angle_beta                 96.81(4)
_cell_angle_gamma                94.96(5)
_cell_formula_units_Z            33
_cell_length_a                   8.036(18)
_cell_length_b                   10.55(2)
_cell_length_c                   13.26(3)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.8
_cell_volume                     1109(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.12
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26748
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.213
_diffrn_reflns_theta_max         25.213
_diffrn_reflns_theta_min         2.396
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       Needle
_exptl_crystal_F_000             462
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       1.7
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0805
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2450
_refine_ls_wR_factor_ref         0.2891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3031
_reflns_number_total             3989
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj00586g2.cif
_cod_data_source_block           MKB_PM_16_XRD_0m_a
_cod_depositor_comments          'Adding full bibliography for 7061479.cif.'
_cod_database_code               7061479
_shelx_shelxl_version_number     2014/7
_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, -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
N1 N 0.7611(2) 0.62406(17) 0.56558(13) 0.0441(5) Uani 1 1 d . . . . .
N2 N 0.6790(2) 0.57107(17) 0.38905(13) 0.0446(5) Uani 1 1 d . . . . .
C20 C 0.7337(3) 0.5428(2) 0.48336(15) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.4592(3) 0.6843(2) 0.09884(16) 0.0398(6) Uani 1 1 d . . . . .
C28 C 0.7735(3) 0.4109(2) 0.49558(16) 0.0444(6) Uani 1 1 d . . . . .
C12 C 0.4855(3) 0.6489(2) 0.20004(16) 0.0384(6) Uani 1 1 d . . . . .
C19 C 0.7256(3) 0.7433(2) 0.55294(16) 0.0433(6) Uani 1 1 d . . . . .
C3 C 0.5994(3) 0.7263(2) 0.27156(16) 0.0420(6) Uani 1 1 d . . . . .
C21 C 0.7620(3) 0.8339(2) 0.64372(17) 0.0433(6) Uani 1 1 d . . . . .
C17 C 0.6453(3) 0.6917(2) 0.37710(17) 0.0424(6) Uani 1 1 d . . . . .
C16 C 0.3486(3) 0.6063(2) 0.02425(17) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.5440(3) 0.7962(2) 0.06979(18) 0.0442(6) Uani 1 1 d . . . . .
C14 C 0.3236(3) 0.6408(2) -0.07754(16) 0.0502(7) Uani 1 1 d . . . . .
C4 C 0.3924(3) 0.5366(2) 0.22570(17) 0.0466(6) Uani 1 1 d . . . . .
H4 H 0.4044 0.5138 0.2926 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2640(3) 0.4939(2) 0.05144(17) 0.0446(6) Uani 1 1 d . . . . .
C18 C 0.6644(3) 0.7801(2) 0.45874(16) 0.0471(6) Uani 1 1 d . . . . .
H18 H 0.6368 0.8630 0.4508 0.056 Uiso 1 1 calc R U . . .
C26 C 0.8901(3) 0.8157(2) 0.71928(17) 0.0489(6) Uani 1 1 d . . . . .
H26 H 0.9493 0.7442 0.7140 0.059 Uiso 1 1 calc R U . . .
C1 C 0.6528(3) 0.8720(2) 0.14321(18) 0.0498(6) Uani 1 1 d . . . . .
H1 H 0.7079 0.9472 0.1258 0.060 Uiso 1 1 calc R U . . .
C2 C 0.6792(3) 0.8364(2) 0.24137(18) 0.0483(6) Uani 1 1 d . . . . .
H2 H 0.7532 0.8882 0.2891 0.058 Uiso 1 1 calc R U . . .
C24 C 0.8453(3) 1.0086(2) 0.81270(18) 0.0525(7) Uani 1 1 d . . . . .
C10 C 0.5154(4) 0.8271(2) -0.03432(19) 0.0556(7) Uani 1 1 d . . . . .
H10 H 0.5713 0.9006 -0.0540 0.067 Uiso 1 1 calc R U . . .
C33 C 0.8673(3) 0.3796(2) 0.58345(18) 0.0525(7) Uani 1 1 d . . . . .
H33 H 0.9033 0.4419 0.6361 0.063 Uiso 1 1 calc R U . . .
C5 C 0.2876(3) 0.4634(2) 0.15431(18) 0.0491(6) Uani 1 1 d . . . . .
H5 H 0.2289 0.3905 0.1731 0.059 Uiso 1 1 calc R U . . .
C22 C 0.6754(3) 0.9397(2) 0.65542(19) 0.0550(7) Uani 1 1 d . . . . .
H22 H 0.5877 0.9535 0.6061 0.066 Uiso 1 1 calc R U . . .
C25 C 0.9303(3) 0.9022(2) 0.80173(19) 0.0557(7) Uani 1 1 d . . . . .
H25 H 1.0173 0.8885 0.8515 0.067 Uiso 1 1 calc R U . . .
C23 C 0.7165(3) 1.0251(2) 0.73876(19) 0.0568(7) Uani 1 1 d . . . . .
H23 H 0.6557 1.0956 0.7452 0.068 Uiso 1 1 calc R U . . .
C29 C 0.7205(3) 0.3165(2) 0.41941(19) 0.0543(7) Uani 1 1 d . . . . .
H29 H 0.6547 0.3354 0.3607 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4116(4) 0.7536(3) -0.10279(19) 0.0617(8) Uani 1 1 d . . . . .
H9 H 0.3961 0.7769 -0.1695 0.074 Uiso 1 1 calc R U . . .
C8 C 0.2167(4) 0.5614(3) -0.14885(19) 0.0620(8) Uani 1 1 d . . . . .
H8 H 0.1994 0.5832 -0.2159 0.074 Uiso 1 1 calc R U . . .
C6 C 0.1580(3) 0.4178(2) -0.0233(2) 0.0560(7) Uani 1 1 d . . . . .
H6 H 0.1013 0.3432 -0.0061 0.067 Uiso 1 1 calc R U . . .
C7 C 0.1361(4) 0.4512(3) -0.1218(2) 0.0630(8) Uani 1 1 d . . . . .
H7 H 0.0657 0.3985 -0.1708 0.076 Uiso 1 1 calc R U . . .
C32 C 0.9072(4) 0.2572(3) 0.5930(2) 0.0659(8) Uani 1 1 d . . . . .
H32 H 0.9690 0.2367 0.6526 0.079 Uiso 1 1 calc R U . . .
C30 C 0.7637(4) 0.1955(2) 0.4293(2) 0.0661(8) Uani 1 1 d . . . . .
H30 H 0.7292 0.1329 0.3767 0.079 Uiso 1 1 calc R U . . .
C31 C 0.8578(4) 0.1650(3) 0.5163(2) 0.0702(9) Uani 1 1 d . . . . .
H31 H 0.8873 0.0823 0.5228 0.084 Uiso 1 1 calc R U . . .
C27 C 0.8909(4) 1.1053(3) 0.9018(2) 0.0749(9) Uani 1 1 d . . . . .
H27A H 0.8357 1.0782 0.9582 0.112 Uiso 1 1 calc R U . . .
H27B H 0.8556 1.1863 0.8834 0.112 Uiso 1 1 calc R U . . .
H27C H 1.0106 1.1133 0.9208 0.112 Uiso 1 1 calc R U . . .
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
C19 N1 C20 116.7(2) . . ?
C20 N2 C17 116.78(19) . . ?
N1 C20 N2 125.9(2) . . ?
N1 C20 C28 117.6(2) . . ?
N2 C20 C28 116.48(19) . . ?
C12 C15 C16 120.3(2) . . ?
C12 C15 C11 120.8(2) . . ?
C16 C15 C11 118.9(2) . . ?
C29 C28 C33 118.7(3) . . ?
C29 C28 C20 120.7(2) . . ?
C33 C28 C20 120.6(2) . . ?
C15 C12 C3 119.0(2) . . ?
C15 C12 C4 118.3(2) . . ?
C3 C12 C4 122.7(2) . . ?
N1 C19 C18 121.2(2) . . ?
N1 C19 C21 116.4(2) . . ?
C18 C19 C21 122.3(2) . . ?
C2 C3 C12 119.0(2) . . ?
C2 C3 C17 118.1(2) . . ?
C12 C3 C17 122.8(2) . . ?
C22 C21 C26 117.9(2) . . ?
C22 C21 C19 122.2(2) . . ?
C26 C21 C19 119.9(2) . . ?
N2 C17 C18 120.9(2) . . ?
N2 C17 C3 116.95(19) . . ?
C18 C17 C3 122.0(2) . . ?
C15 C16 C13 119.8(2) . . ?
C15 C16 C14 120.4(2) . . ?
C13 C16 C14 119.8(2) . . ?
C1 C11 C15 118.6(2) . . ?
C1 C11 C10 122.6(2) . . ?
C15 C11 C10 118.8(2) . . ?
C8 C14 C16 118.9(3) . . ?
C8 C14 C9 122.5(3) . . ?
C16 C14 C9 118.5(2) . . ?
C5 C4 C12 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C12 C4 H4 119.6 . . ?
C6 C13 C16 118.9(3) . . ?
C6 C13 C5 122.4(3) . . ?
C16 C13 C5 118.7(2) . . ?
C17 C18 C19 118.4(2) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C2 C1 C11 120.3(2) . . ?
C2 C1 H1 119.8 . . ?
C11 C1 H1 119.8 . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C25 C24 C23 117.8(2) . . ?
C25 C24 C27 121.9(3) . . ?
C23 C24 C27 120.3(3) . . ?
C9 C10 C11 121.6(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C32 C33 C28 120.1(2) . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
C4 C5 C13 121.9(2) . . ?
C4 C5 H5 119.0 . . ?
C13 C5 H5 119.0 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C26 C25 C24 121.6(3) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C22 C23 C24 121.3(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C10 C9 C14 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C14 C9 H9 119.1 . . ?
C14 C8 C7 120.8(3) . . ?
C14 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C6 C13 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C13 C6 H6 119.5 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C33 C32 C31 120.9(3) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C29 C30 C31 120.6(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 119.2(3) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
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
N1 C19 1.331(4) . ?
N1 C20 1.329(3) . ?
N2 C20 1.336(4) . ?
N2 C17 1.339(4) . ?
C20 C28 1.469(4) . ?
C15 C12 1.411(4) . ?
C15 C16 1.417(4) . ?
C15 C11 1.410(4) . ?
C28 C29 1.376(4) . ?
C28 C33 1.385(4) . ?
C12 C3 1.404(4) . ?
C12 C4 1.427(4) . ?
C19 C18 1.378(4) . ?
C19 C21 1.474(4) . ?
C3 C2 1.382(4) . ?
C3 C17 1.480(4) . ?
C21 C22 1.376(4) . ?
C21 C26 1.383(4) . ?
C17 C18 1.370(4) . ?
C16 C13 1.403(4) . ?
C16 C14 1.415(4) . ?
C11 C1 1.390(4) . ?
C11 C10 1.435(4) . ?
C14 C8 1.385(4) . ?
C14 C9 1.411(4) . ?
C4 C5 1.346(4) . ?
C4 H4 0.9300 . ?
C13 C6 1.391(4) . ?
C13 C5 1.416(4) . ?
C18 H18 0.9300 . ?
C26 C25 1.369(4) . ?
C26 H26 0.9300 . ?
C1 C2 1.374(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C24 C25 1.372(4) . ?
C24 C23 1.369(4) . ?
C24 C27 1.502(4) . ?
C10 C9 1.320(4) . ?
C10 H10 0.9300 . ?
C33 C32 1.367(5) . ?
C33 H33 0.9300 . ?
C5 H5 0.9300 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?
C23 H23 0.9300 . ?
C29 C30 1.362(5) . ?
C29 H29 0.9300 . ?
C9 H9 0.9300 . ?
C8 C7 1.370(5) . ?
C8 H8 0.9300 . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C32 C31 1.361(5) . ?
C32 H32 0.9300 . ?
C30 C31 1.374(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
