#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215548.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215548
loop_
_publ_author_name
'He, Wei'
'Sun, Hong-Shun'
'Xu, Ye-ming'
'Tang, Shi-gui'
'Guo, Cheng'
_publ_section_title
;
 Methyl
 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carboxylate
;
_journal_coeditor_code           HK2328
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4157
_journal_page_last               o4157
_journal_paper_doi               10.1107/S1600536807046181
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H18 F N3 O2'
_chemical_formula_moiety         'C16 H18 F N3 O2'
_chemical_formula_sum            'C16 H18 F N3 O2'
_chemical_formula_weight         303.33
_chemical_name_systematic
;
Methyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 102.51(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.900(3)
_cell_length_b                   8.6750(17)
_cell_length_c                   14.775(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1614.2(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Siemens, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3308
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.607
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3165
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1660
_refine_ls_R_factor_gt           0.0890
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.04P)²+2.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.2008
_reflns_number_gt                1547
_reflns_number_total             3165
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2328.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215548
_cod_database_fobs_code          2215548
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
F F 0.6304(3) 0.6065(4) -0.0554(2) 0.101 Uani d . 1
O O1 0.5706(3) -0.0685(5) 0.1532(3) 0.0833(12) Uani d . 1
O O2 0.6494(2) 0.1523(4) 0.2054(2) 0.0643(9) Uani d . 1
N N1 0.8941(2) 0.0035(4) 0.0741(2) 0.0415(8) Uani d . 1
N N2 0.9043(3) -0.2017(4) 0.1841(2) 0.0500(9) Uani d . 1
N N3 1.0321(3) -0.1679(4) 0.1009(2) 0.0563(10) Uani d . 1
H H3A 1.0530 -0.1223 0.0563 0.068 Uiso calc R 1
C C1 0.6090(5) 0.3378(8) -0.0376(4) 0.0944(18) Uani d DU 1
H H1A 0.5390 0.3451 -0.0704 0.113 Uiso calc R 1
C C2 0.6747(5) 0.4669(7) -0.0202(4) 0.0786(16) Uani d DU 1
C C3 0.7757(5) 0.4633(6) 0.0259(4) 0.0760(15) Uani d DU 1
H H3B 0.8170 0.5522 0.0345 0.091 Uiso calc R 1
C C4 0.8161(4) 0.3257(5) 0.0599(3) 0.0562(12) Uani d DU 1
H H4A 0.8862 0.3202 0.0925 0.067 Uiso calc R 1
C C5 0.7545(3) 0.1920(5) 0.0468(3) 0.0481(11) Uani d DU 1
C C6 0.6536(4) 0.1955(7) -0.0030(3) 0.0693(14) Uani d DU 1
H H6A 0.6140 0.1053 -0.0143 0.083 Uiso calc R 1
C C7 0.8023(3) 0.0461(5) 0.0918(3) 0.0417(10) Uani d . 1
C C8 0.9410(3) -0.1220(5) 0.1200(3) 0.0445(10) Uani d . 1
C C9 1.0985(4) -0.2888(6) 0.1494(4) 0.0800(17) Uani d . 1
H H9A 1.1608 -0.2993 0.1243 0.120 Uiso calc R 1
H H9B 1.0599 -0.3842 0.1422 0.120 Uiso calc R 1
H H9C 1.1190 -0.2633 0.2141 0.120 Uiso calc R 1
C C10 0.8103(3) -0.1588(5) 0.1997(3) 0.0478(11) Uani d . 1
C C11 0.7731(4) -0.2473(5) 0.2754(3) 0.0576(12) Uani d . 1
H H11A 0.7137 -0.1901 0.2907 0.069 Uiso calc R 1
C C12 0.8595(4) -0.2599(6) 0.3634(3) 0.0782(16) Uani d . 1
H H12A 0.8852 -0.1588 0.3830 0.117 Uiso calc R 1
H H12B 0.9169 -0.3214 0.3514 0.117 Uiso calc R 1
H H12C 0.8308 -0.3074 0.4113 0.117 Uiso calc R 1
C C13 0.7324(5) -0.4065(7) 0.2423(4) 0.0943(19) Uani d . 1
H H13A 0.6761 -0.3967 0.1882 0.141 Uiso calc R 1
H H13B 0.7061 -0.4575 0.2905 0.141 Uiso calc R 1
H H13C 0.7892 -0.4658 0.2274 0.141 Uiso calc R 1
C C14 0.7545(3) -0.0341(5) 0.1540(3) 0.0443(10) Uani d . 1
C C15 0.6489(4) 0.0108(6) 0.1706(3) 0.0552(12) Uani d . 1
C C16 0.5490(4) 0.2113(8) 0.2158(5) 0.099(2) Uani d . 1
H H16A 0.5584 0.3131 0.2419 0.149 Uiso calc R 1
H H16B 0.5202 0.1450 0.2563 0.149 Uiso calc R 1
H H16C 0.5010 0.2154 0.1563 0.149 Uiso calc R 1
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'
F F 0.0171 0.0103 '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
C15 O2 C16 116.2(4)
C7 N1 C8 116.7(3)
C10 N2 C8 116.8(4)
C8 N3 C9 124.7(4)
C8 N3 H3A 117.6
C9 N3 H3A 117.6
C2 C1 C6 116.9(5)
C2 C1 H1A 121.6
C6 C1 H1A 121.6
C3 C2 F 119.2(6)
C3 C2 C1 124.2(5)
F C2 C1 116.5(5)
C2 C3 C4 117.7(5)
C2 C3 H3B 121.2
C4 C3 H3B 121.2
C3 C4 C5 121.3(5)
C3 C4 H4A 119.3
C5 C4 H4A 119.4
C6 C5 C4 120.7(4)
C6 C5 C7 121.1(4)
C4 C5 C7 118.2(4)
C5 C6 C1 119.1(5)
C5 C6 H6A 120.4
C1 C6 H6A 120.4
N1 C7 C14 122.2(4)
N1 C7 C5 116.7(3)
C14 C7 C5 120.9(4)
N3 C8 N2 117.4(4)
N3 C8 N1 117.1(4)
N2 C8 N1 125.5(4)
N3 C9 H9A 109.5
N3 C9 H9B 109.5
H9A C9 H9B 109.5
N3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N2 C10 C14 121.9(4)
N2 C10 C11 115.4(4)
C14 C10 C11 122.5(4)
C10 C11 C13 111.4(4)
C10 C11 C12 112.0(4)
C13 C11 C12 110.3(4)
C10 C11 H11A 107.6
C13 C11 H11A 107.6
C12 C11 H11A 107.6
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C10 C14 C7 116.7(4)
C10 C14 C15 121.4(4)
C7 C14 C15 121.9(4)
O1 C15 O2 123.0(4)
O1 C15 C14 124.8(5)
O2 C15 C14 112.2(4)
O2 C16 H16A 109.5
O2 C16 H16B 109.5
H16A C16 H16B 109.5
O2 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F C2 1.390(5)
O1 C15 1.203(5)
O2 C15 1.331(6)
O2 C16 1.432(5)
N1 C7 1.319(5)
N1 C8 1.354(5)
N2 C10 1.335(5)
N2 C8 1.340(5)
N3 C8 1.328(5)
N3 C9 1.443(5)
N3 H3A 0.8600
C1 C2 1.395(8)
C1 C6 1.410(7)
C1 H1A 0.9300
C2 C3 1.334(7)
C3 C4 1.354(6)
C3 H3B 0.9300
C4 C5 1.395(6)
C4 H4A 0.9300
C5 C6 1.349(6)
C5 C7 1.499(6)
C6 H6A 0.9300
C7 C14 1.399(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C14 1.390(5)
C10 C11 1.518(6)
C11 C13 1.519(7)
C11 C12 1.523(6)
C11 H11A 0.9800
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.488(6)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A N1 3_755 0.86 2.41 3.270(4) 177.0
C16 H16C F 3_665 0.96 2.53 3.331(8) 141.0
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
C6 C1 C2 C3 0.4(8)
C6 C1 C2 F 179.3(4)
F C2 C3 C4 179.6(4)
C1 C2 C3 C4 -1.6(8)
C2 C3 C4 C5 0.3(7)
C3 C4 C5 C6 2.3(7)
C3 C4 C5 C7 -175.9(4)
C4 C5 C6 C1 -3.4(7)
C7 C5 C6 C1 174.7(4)
C2 C1 C6 C5 2.1(7)
C8 N1 C7 C14 -0.6(5)
C8 N1 C7 C5 175.4(3)
C6 C5 C7 N1 127.6(4)
C4 C5 C7 N1 -54.2(5)
C6 C5 C7 C14 -56.3(6)
C4 C5 C7 C14 121.9(4)
C9 N3 C8 N2 -5.4(7)
C9 N3 C8 N1 173.3(4)
C10 N2 C8 N3 -177.1(4)
C10 N2 C8 N1 4.3(6)
C7 N1 C8 N3 178.4(4)
C7 N1 C8 N2 -3.0(6)
C8 N2 C10 C14 -2.1(6)
C8 N2 C10 C11 -177.7(4)
N2 C10 C11 C13 -76.0(5)
C14 C10 C11 C13 108.4(5)
N2 C10 C11 C12 48.1(6)
C14 C10 C11 C12 -127.4(5)
N2 C10 C14 C7 -1.0(6)
C11 C10 C14 C7 174.3(4)
N2 C10 C14 C15 178.8(4)
C11 C10 C14 C15 -5.9(6)
N1 C7 C14 C10 2.5(6)
C5 C7 C14 C10 -173.4(4)
N1 C7 C14 C15 -177.4(4)
C5 C7 C14 C15 6.8(6)
C16 O2 C15 O1 -4.1(7)
C16 O2 C15 C14 174.5(4)
C10 C14 C15 O1 -63.2(6)
C7 C14 C15 O1 116.6(5)
C10 C14 C15 O2 118.3(4)
C7 C14 C15 O2 -61.9(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16485230
2 PubChem 17989605
