#------------------------------------------------------------------------------
#$Date: 2017-09-12 07:01:55 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200727 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/67/1546792.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_1546792
loop_
_publ_author_name
'Meng, Guangrong'
'Lalancette, Roger'
'Szostak, Roman'
'Szostak, Michal'
_publ_section_title
;
 N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive,
 Electronically-Activated Amides in Catalytic N-C(O) Cleavage.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4656
_journal_page_last               4659
_journal_paper_doi               10.1021/acs.orglett.7b02288
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                98.93(2)
_cell_angle_beta                 102.72(3)
_cell_angle_gamma                107.148(17)
_cell_formula_units_Z            2
_cell_length_a                   6.0966(16)
_cell_length_b                   8.7275(19)
_cell_length_c                   11.867(4)
_cell_measurement_reflns_used    4649
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.07
_cell_measurement_theta_min      3.93
_cell_volume                     571.9(3)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.920
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5382
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.184
_diffrn_reflns_theta_min         3.930
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.284
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0134(12)
_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   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0322
_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)+(0.0408P)²+0.2486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1848
_reflns_number_total             1923
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b02288_si_002.cif
_cod_data_source_block           170413RAL_MENG_PYRIMIDINE_100K_0m_a
_cod_depositor_comments          'Adding full bibliography for 1546792.cif.'
_cod_database_code               1546792
_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
O1 O 1.00231(15) 0.61441(10) 0.83012(7) 0.0204(2) Uani 1 1 d . .
N1 N 0.96671(16) 0.35672(11) 0.85596(8) 0.0150(2) Uani 1 1 d . .
N2 N 0.59023(17) 0.18830(12) 0.85619(8) 0.0154(2) Uani 1 1 d . .
N3 N 0.90964(17) 0.08178(12) 0.85778(9) 0.0169(2) Uani 1 1 d . .
C2 C 0.8133(2) 0.20009(14) 0.85514(10) 0.0136(3) Uani 1 1 d . .
C4 C 0.6651(2) 0.39718(14) 0.69886(10) 0.0157(3) Uani 1 1 d . .
C11 C 0.4471(2) 0.03834(14) 0.85326(10) 0.0166(3) Uani 1 1 d . .
H11 H 0.2852 0.0227 0.8512 0.020 Uiso 1 1 calc R U
C1 C 0.8878(2) 0.46637(14) 0.80100(10) 0.0154(3) Uani 1 1 d . .
C13 C 0.7623(2) -0.06628(14) 0.85769(11) 0.0181(3) Uani 1 1 d . .
H13 H 0.8233 -0.1544 0.8609 0.022 Uiso 1 1 calc R U
C9 C 0.4959(2) 0.47501(14) 0.68765(11) 0.0181(3) Uani 1 1 d . .
H9 H 0.5229 0.5730 0.7445 0.022 Uiso 1 1 calc R U
C5 C 0.6289(2) 0.25881(15) 0.61138(11) 0.0182(3) Uani 1 1 d . .
H5 H 0.7453 0.2059 0.6167 0.022 Uiso 1 1 calc R U
C3 C 1.21726(19) 0.40860(14) 0.92723(10) 0.0169(3) Uani 1 1 d . .
H3A H 1.3101 0.3684 0.8795 0.025 Uiso 1 1 calc R U
H3B H 1.2255 0.3626 0.9977 0.025 Uiso 1 1 calc R U
H3C H 1.2833 0.5293 0.9520 0.025 Uiso 1 1 calc R U
C12 C 0.5247(2) -0.09583(14) 0.85313(10) 0.0181(3) Uani 1 1 d . .
H12 H 0.4201 -0.2024 0.8501 0.022 Uiso 1 1 calc R U
C6 C 0.4232(2) 0.19812(15) 0.51651(11) 0.0199(3) Uani 1 1 d . .
H6 H 0.4023 0.1052 0.4564 0.024 Uiso 1 1 calc R U
C8 C 0.2876(2) 0.41102(15) 0.59414(11) 0.0198(3) Uani 1 1 d . .
H8 H 0.1712 0.4638 0.5891 0.024 Uiso 1 1 calc R U
C7 C 0.2469(2) 0.27040(15) 0.50750(11) 0.0192(3) Uani 1 1 d . .
C10 C 0.0204(2) 0.19993(17) 0.40594(11) 0.0249(3) Uani 1 1 d . .
H10A H -0.1102 0.2243 0.4318 0.037 Uiso 1 1 calc R U
H10B H -0.0204 0.0802 0.3810 0.037 Uiso 1 1 calc R U
H10C H 0.0447 0.2496 0.3390 0.037 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C2 122.91(10)
C1 N1 C3 119.31(10)
C2 N1 C3 117.58(9)
C11 N2 C2 115.41(10)
C2 N3 C13 115.58(10)
N3 C2 N2 127.31(11)
N3 C2 N1 116.19(10)
N2 C2 N1 116.45(10)
C9 C4 C5 118.98(11)
C9 C4 C1 120.04(11)
C5 C4 C1 120.92(11)
N2 C11 C12 122.71(11)
N2 C11 H11 118.6
C12 C11 H11 118.6
O1 C1 N1 121.33(11)
O1 C1 C4 120.86(11)
N1 C1 C4 117.69(10)
N3 C13 C12 122.47(11)
N3 C13 H13 118.8
C12 C13 H13 118.8
C4 C9 C8 120.58(11)
C4 C9 H9 119.7
C8 C9 H9 119.7
C4 C5 C6 120.05(12)
C4 C5 H5 120.0
C6 C5 H5 120.0
N1 C3 H3A 109.5
N1 C3 H3B 109.5
H3A C3 H3B 109.5
N1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C13 C12 C11 116.42(11)
C13 C12 H12 121.8
C11 C12 H12 121.8
C5 C6 C7 121.41(11)
C5 C6 H6 119.3
C7 C6 H6 119.3
C9 C8 C7 120.89(12)
C9 C8 H8 119.6
C7 C8 H8 119.6
C8 C7 C6 117.98(12)
C8 C7 C10 121.11(12)
C6 C7 C10 120.90(12)
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2246(14)
N1 C1 1.3784(16)
N1 C2 1.4076(15)
N1 C3 1.4690(15)
N2 C11 1.3322(16)
N2 C2 1.3364(15)
N3 C2 1.3309(16)
N3 C13 1.3386(16)
C4 C9 1.3869(18)
C4 C5 1.3920(17)
C4 C1 1.4971(18)
C11 C12 1.3861(17)
C11 H11 0.9500
C13 C12 1.3815(17)
C13 H13 0.9500
C9 C8 1.3874(19)
C9 H9 0.9500
C5 C6 1.3863(19)
C5 H5 0.9500
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C12 H12 0.9500
C6 C7 1.3910(18)
C6 H6 0.9500
C8 C7 1.3933(18)
C8 H8 0.9500
C7 C10 1.5080(18)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
