#------------------------------------------------------------------------------
#$Date: 2018-09-08 21:34:38 +0300 (Sat, 08 Sep 2018) $
#$Revision: 210577 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/48/7104883.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_7104883
loop_
_publ_author_name
'Brough, P.'
'Chiarelli, R.'
'Pécaut, J.'
'Rassat, A.'
'Rey, P.'
_publ_section_title
;
 A versatile synthesis of new pyrimidinyl nitronyl nitroxides
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   21
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2722
_journal_page_last               2723
_journal_paper_doi               10.1039/b309786b
_journal_year                    2003
_chemical_formula_sum            'C14 H19 N2 O2'
_chemical_formula_weight         247.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.862(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2438(5)
_cell_length_b                   21.3603(17)
_cell_length_c                   9.9984(8)
_cell_measurement_temperature    298(2)
_cell_volume                     1323.93(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6664
_diffrn_reflns_theta_full        28.92
_diffrn_reflns_theta_max         28.92
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                1835
_reflns_number_total             3093
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b309786b.txt
_cod_data_source_block           struc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7104883
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23852(17) 0.04139(5) 0.64731(9) 0.0482(3) Uani 1 1 d . . .
O2 O 0.66330(19) 0.21502(5) 0.70269(10) 0.0606(4) Uani 1 1 d . . .
N1 N 0.30840(18) 0.09232(5) 0.59655(11) 0.0321(3) Uani 1 1 d . . .
N2 N 0.51941(18) 0.18343(5) 0.62812(10) 0.0349(3) Uani 1 1 d . . .
C1 C 0.4588(2) 0.12687(6) 0.67100(13) 0.0289(3) Uani 1 1 d . . .
C2 C 0.2156(2) 0.10734(6) 0.45511(12) 0.0300(3) Uani 1 1 d . . .
C3 C 0.3388(2) 0.16285(7) 0.40521(14) 0.0317(3) Uani 1 1 d . . .
H3A H 0.252(2) 0.1811(6) 0.3311(14) 0.038(4) Uiso 1 1 d . . .
H3B H 0.472(2) 0.1471(6) 0.3707(12) 0.034(4) Uiso 1 1 d . . .
C4 C 0.4055(2) 0.21494(6) 0.50568(13) 0.0321(3) Uani 1 1 d . . .
C5 C -0.0263(3) 0.11836(9) 0.45437(19) 0.0442(4) Uani 1 1 d . . .
H5A H -0.096(3) 0.0809(9) 0.4754(17) 0.068(6) Uiso 1 1 d . . .
H5B H -0.090(3) 0.1304(8) 0.3634(17) 0.060(5) Uiso 1 1 d . . .
H5C H -0.053(3) 0.1514(8) 0.5230(17) 0.064(5) Uiso 1 1 d . . .
C6 C 0.2495(3) 0.04965(8) 0.37026(17) 0.0449(4) Uani 1 1 d . . .
H6A H 0.178(3) 0.0125(8) 0.4007(15) 0.061(5) Uiso 1 1 d . . .
H6B H 0.408(3) 0.0414(7) 0.3740(14) 0.053(5) Uiso 1 1 d . . .
H6C H 0.193(2) 0.0589(7) 0.2743(17) 0.051(4) Uiso 1 1 d . . .
C7 C 0.2208(3) 0.25241(8) 0.55281(19) 0.0461(4) Uani 1 1 d . . .
H7A H 0.134(3) 0.2711(8) 0.4781(16) 0.066(5) Uiso 1 1 d . . .
H7B H 0.280(2) 0.2869(8) 0.6123(15) 0.058(5) Uiso 1 1 d . . .
H7C H 0.128(3) 0.2263(8) 0.6053(15) 0.051(5) Uiso 1 1 d . . .
C8 C 0.5630(3) 0.25855(8) 0.44746(18) 0.0424(4) Uani 1 1 d . . .
H8A H 0.688(3) 0.2339(8) 0.4190(16) 0.065(5) Uiso 1 1 d . . .
H8B H 0.614(3) 0.2895(8) 0.5099(15) 0.061(5) Uiso 1 1 d . . .
H8C H 0.484(2) 0.2781(7) 0.3687(15) 0.045(4) Uiso 1 1 d . . .
C9 C 0.5477(2) 0.10469(6) 0.80713(13) 0.0276(3) Uani 1 1 d . . .
C10 C 0.7613(2) 0.08727(6) 0.83548(16) 0.0356(4) Uani 1 1 d . . .
H10 H 0.855(2) 0.0882(6) 0.7651(15) 0.041(4) Uiso 1 1 d . . .
C11 C 0.8400(3) 0.06796(7) 0.96421(17) 0.0453(4) Uani 1 1 d . . .
H11 H 0.988(3) 0.0559(7) 0.9792(16) 0.054(5) Uiso 1 1 d . . .
C12 C 0.7060(3) 0.06610(7) 1.06394(17) 0.0511(5) Uani 1 1 d . . .
H12 H 0.762(2) 0.0522(8) 1.1497(16) 0.056(5) Uiso 1 1 d . . .
C13 C 0.4960(3) 0.08417(8) 1.03607(16) 0.0509(5) Uani 1 1 d . . .
H13 H 0.400(3) 0.0839(8) 1.1046(19) 0.067(6) Uiso 1 1 d . . .
C14 C 0.4155(3) 0.10357(7) 0.90849(15) 0.0399(4) Uani 1 1 d . . .
H14 H 0.275(3) 0.1158(7) 0.8916(15) 0.051(5) Uiso 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
O1 N1 C1 119.21(10) . . ?
O1 N1 C2 116.02(10) . . ?
C1 N1 C2 124.75(11) . . ?
O2 N2 C1 119.17(10) . . ?
O2 N2 C4 117.87(10) . . ?
C1 N2 C4 122.47(10) . . ?
N1 C1 N2 121.20(11) . . ?
N1 C1 C9 119.44(11) . . ?
N2 C1 C9 119.20(11) . . ?
N1 C2 C6 106.77(12) . . ?
N1 C2 C5 107.95(12) . . ?
C6 C2 C5 108.93(13) . . ?
N1 C2 C3 108.75(10) . . ?
C6 C2 C3 109.67(12) . . ?
C5 C2 C3 114.49(12) . . ?
C4 C3 C2 117.37(12) . . ?
N2 C4 C8 108.80(11) . . ?
N2 C4 C3 106.02(11) . . ?
C8 C4 C3 109.48(13) . . ?
N2 C4 C7 106.60(12) . . ?
C8 C4 C7 110.17(13) . . ?
C3 C4 C7 115.47(12) . . ?
C10 C9 C14 119.46(13) . . ?
C10 C9 C1 121.35(13) . . ?
C14 C9 C1 119.15(13) . . ?
C9 C10 C11 119.86(16) . . ?
C12 C11 C10 120.18(16) . . ?
C13 C12 C11 119.79(15) . . ?
C12 C13 C14 120.68(18) . . ?
C13 C14 C9 120.01(16) . . ?
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
O1 N1 1.2979(14) . ?
O2 N2 1.2877(13) . ?
N1 C1 1.3465(16) . ?
N1 C2 1.4975(16) . ?
N2 C1 1.3511(17) . ?
N2 C4 1.4997(16) . ?
C1 C9 1.4849(17) . ?
C2 C6 1.525(2) . ?
C2 C5 1.528(2) . ?
C2 C3 1.5291(19) . ?
C3 C4 1.5234(19) . ?
C4 C8 1.520(2) . ?
C4 C7 1.524(2) . ?
C9 C10 1.3812(19) . ?
C9 C14 1.382(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.377(3) . ?
C12 C13 1.363(3) . ?
C13 C14 1.378(2) . ?
