#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/50/48/1504883.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_1504883
loop_
_publ_author_name
'Anderson, James C.'
'Blake, Alexander J.'
'Mills, Matthew'
'Ratcliffe, Paul D.'
_publ_section_title
;
 A general one-step synthesis of beta-nitronitriles.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4141
_journal_page_last               4143
_journal_paper_doi               10.1021/ol801691c
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C8 H12 N2 O2'
_chemical_formula_sum            'C8 H12 N2 O2'
_chemical_formula_weight         168.20
_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
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.508(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8362(12)
_cell_length_b                   9.600(2)
_cell_length_c                   12.054(2)
_cell_measurement_reflns_used    2318
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.7
_cell_volume                     900.9(3)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5655
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.11
_refine_diff_density_rms         0.04
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0427
_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/[\s^2^(Fo^2^)+(0.069P)^2^+0.028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.116
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                1664
_reflns_number_total             2049
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ol801691c_si_002.cif
_cod_data_source_block           nocncx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'placed geometrically' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        900.9(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504883
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_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
N1 N 0.76624(13) 0.05245(10) 0.44119(8) 0.0359(3) Uani 1 1 d .
O1 O 0.79648(15) 0.06221(9) 0.54270(7) 0.0534(3) Uani 1 1 d .
O2 O 0.72292(16) -0.05518(10) 0.39331(9) 0.0633(3) Uani 1 1 d .
C1 C 0.78549(14) 0.18101(11) 0.37188(8) 0.0294(3) Uani 1 1 d .
H1A H 0.7713 0.1525 0.2916 0.035 Uiso 1 1 calc R
C2 C 0.64332(13) 0.28726(11) 0.38862(8) 0.0274(3) Uani 1 1 d .
C3 C 0.66954(14) 0.41208(12) 0.31103(9) 0.0317(3) Uani 1 1 d .
H3A H 0.6494 0.3808 0.2324 0.038 Uiso 1 1 calc R
H3B H 0.5835 0.4849 0.3221 0.038 Uiso 1 1 calc R
C4 C 0.84790(16) 0.47465(13) 0.33233(11) 0.0405(3) Uani 1 1 d .
H4A H 0.8642 0.5151 0.4084 0.049 Uiso 1 1 calc R
H4B H 0.8594 0.5507 0.2782 0.049 Uiso 1 1 calc R
C5 C 0.98549(16) 0.36570(15) 0.32137(11) 0.0459(3) Uani 1 1 d .
H5A H 1.1002 0.4080 0.3405 0.055 Uiso 1 1 calc R
H5B H 0.9776 0.3331 0.2430 0.055 Uiso 1 1 calc R
C6 C 0.96541(15) 0.24148(13) 0.39824(10) 0.0379(3) Uani 1 1 d .
H6A H 1.0523 0.1696 0.3868 0.045 Uiso 1 1 calc R
H6B H 0.9834 0.2718 0.4772 0.045 Uiso 1 1 calc R
C7 C 0.66025(14) 0.33876(12) 0.50483(9) 0.0319(3) Uani 1 1 d .
N2 N 0.66896(15) 0.38378(12) 0.59288(8) 0.0461(3) Uani 1 1 d .
C8 C 0.46319(15) 0.22617(14) 0.35961(11) 0.0435(3) Uani 1 1 d .
H8A H 0.4474 0.1473 0.4090 0.065 Uiso 1 1 calc R
H8B H 0.4498 0.1944 0.2819 0.065 Uiso 1 1 calc R
H8C H 0.3771 0.2978 0.3694 0.065 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0453(6) 0.0298(5) 0.0335(6) 0.0020(4) 0.0082(4) 0.0063(4)
O1 0.0912(8) 0.0400(5) 0.0303(5) 0.0078(4) 0.0126(5) 0.0112(5)
O2 0.0986(9) 0.0323(5) 0.0572(7) -0.0017(4) 0.0013(6) -0.0105(5)
C1 0.0386(6) 0.0279(6) 0.0223(5) 0.0011(4) 0.0061(4) 0.0061(4)
C2 0.0303(5) 0.0287(5) 0.0236(5) 0.0002(4) 0.0052(4) 0.0020(4)
C3 0.0376(6) 0.0323(6) 0.0256(6) 0.0050(4) 0.0051(4) 0.0054(5)
C4 0.0447(7) 0.0358(7) 0.0423(7) 0.0093(5) 0.0098(5) -0.0032(5)
C5 0.0347(6) 0.0529(8) 0.0519(8) 0.0120(6) 0.0129(5) -0.0014(6)
C6 0.0314(6) 0.0436(7) 0.0392(7) 0.0042(5) 0.0068(5) 0.0086(5)
C7 0.0385(6) 0.0302(6) 0.0285(6) 0.0028(4) 0.0095(4) 0.0054(5)
N2 0.0664(7) 0.0450(6) 0.0279(5) -0.0017(5) 0.0103(5) 0.0139(5)
C8 0.0343(6) 0.0436(7) 0.0522(8) -0.0006(6) 0.0034(5) -0.0039(5)
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
O2 N1 O1 123.59(10)
O2 N1 C1 118.28(10)
O1 N1 C1 118.13(9)
N1 C1 C6 110.15(9)
N1 C1 C2 110.49(8)
C6 C1 C2 112.71(9)
N1 C1 H1A 107.8
C6 C1 H1A 107.8
C2 C1 H1A 107.8
C7 C2 C8 109.03(9)
C7 C2 C1 110.93(9)
C8 C2 C1 112.21(9)
C7 C2 C3 108.06(9)
C8 C2 C3 109.90(9)
C1 C2 C3 106.61(8)
C4 C3 C2 112.79(9)
C4 C3 H3A 109.0
C2 C3 H3A 109.0
C4 C3 H3B 109.0
C2 C3 H3B 109.0
H3A C3 H3B 107.8
C3 C4 C5 111.25(10)
C3 C4 H4A 109.4
C5 C4 H4A 109.4
C3 C4 H4B 109.4
C5 C4 H4B 109.4
H4A C4 H4B 108.0
C4 C5 C6 111.20(10)
C4 C5 H5A 109.4
C6 C5 H5A 109.4
C4 C5 H5B 109.4
C6 C5 H5B 109.4
H5A C5 H5B 108.0
C1 C6 C5 109.08(9)
C1 C6 H6A 109.9
C5 C6 H6A 109.9
C1 C6 H6B 109.9
C5 C6 H6B 109.9
H6A C6 H6B 108.3
N2 C7 C2 176.83(12)
C2 C8 H8A 109.5
C2 C8 H8B 109.5
H8A C8 H8B 109.5
C2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O2 1.2132(13)
N1 O1 1.2232(13)
N1 C1 1.5076(14)
C1 C6 1.5245(16)
C1 C2 1.5405(15)
C1 H1A 1.0000
C2 C7 1.4772(15)
C2 C8 1.5319(16)
C2 C3 1.5480(14)
C3 C4 1.5162(17)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.5186(18)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5292(17)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 N2 1.1409(14)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
O2 N1 C1 C6 -124.03(12)
O1 N1 C1 C6 55.43(13)
O2 N1 C1 C2 110.80(12)
O1 N1 C1 C2 -69.75(13)
N1 C1 C2 C7 64.78(11)
C6 C1 C2 C7 -58.93(11)
N1 C1 C2 C8 -57.44(12)
C6 C1 C2 C8 178.85(9)
N1 C1 C2 C3 -177.80(8)
C6 C1 C2 C3 58.49(11)
C7 C2 C3 C4 63.20(11)
C8 C2 C3 C4 -177.94(10)
C1 C2 C3 C4 -56.10(12)
C2 C3 C4 C5 56.30(13)
C3 C4 C5 C6 -55.39(14)
N1 C1 C6 C5 176.22(9)
C2 C1 C6 C5 -59.88(12)
C4 C5 C6 C1 56.47(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 25099107
