#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:42:11 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243556 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/62/1556201.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_1556201
loop_
_publ_author_name
'Maity, Soham'
'Naveen, Togati'
'Sharma, Upendra'
'Maiti, Debabrata'
_publ_section_title
;
 Stereoselective nitration of olefins with (t)BuONO and TEMPO: direct
 access to nitroolefins under metal-free conditions.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3384
_journal_page_last               3387
_journal_paper_doi               10.1021/ol401426p
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C11 H9 N O3'
_chemical_formula_weight         203.19
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 98.050(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2107(19)
_cell_length_b                   11.437(3)
_cell_length_c                   11.361(3)
_cell_measurement_temperature    373(2)
_cell_volume                     927.7(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6546
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.56
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.168
_refine_diff_density_min         -0.965
_refine_diff_density_rms         0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0828
_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)+(0.3000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2818
_refine_ls_wR_factor_ref         0.3630
_reflns_number_gt                1416
_reflns_number_total             1611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401426p_si_003.cif
_cod_data_source_block           opsD
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1556201
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
O3 O 0.3100(3) 0.96392(17) 0.07037(17) 0.0198(8) Uani 1 1 d .
O2 O 0.1649(3) 0.6159(2) -0.1839(2) 0.0330(8) Uani 1 1 d .
N1 N 0.2207(4) 0.6381(2) -0.0792(2) 0.0243(9) Uani 1 1 d .
O1 O 0.2639(4) 0.5616(2) -0.0041(2) 0.0457(10) Uani 1 1 d .
C1 C 0.2212(4) 0.9641(2) -0.0462(3) 0.0179(9) Uani 1 1 d .
C3 C 0.2481(3) 1.1514(2) 0.0101(2) 0.0181(9) Uani 1 1 d .
C10 C 0.2418(4) 0.7570(2) -0.0384(3) 0.0194(9) Uani 1 1 d .
H10 H 0.2977 0.7691 0.0395 0.023 Uiso 1 1 calc R
C6 C 0.4022(4) 1.2408(3) 0.2291(3) 0.0211(9) Uani 1 1 d .
H6 H 0.4508 1.2728 0.3022 0.025 Uiso 1 1 calc R
C7 C 0.4037(4) 1.1202(3) 0.2150(2) 0.0204(9) Uani 1 1 d .
H7 H 0.4544 1.0701 0.2756 0.024 Uiso 1 1 calc R
C2 C 0.1811(4) 1.0747(2) -0.0845(2) 0.0180(8) Uani 1 1 d .
H2 H 0.1207 1.0963 -0.1591 0.022 Uiso 1 1 calc R
C9 C 0.1873(4) 0.8515(2) -0.1037(3) 0.0183(9) Uani 1 1 d .
C5 C 0.3293(4) 1.3158(2) 0.1361(3) 0.0227(9) Uani 1 1 d .
H5 H 0.3347 1.3962 0.1484 0.027 Uiso 1 1 calc R
C8 C 0.3239(4) 1.0798(2) 0.1041(3) 0.0188(9) Uani 1 1 d .
C4 C 0.2504(4) 1.2736(3) 0.0273(3) 0.0216(9) Uani 1 1 d .
H4 H 0.2001 1.3240 -0.0331 0.026 Uiso 1 1 calc R
C11 C 0.0933(4) 0.8531(3) -0.2305(3) 0.0239(9) Uani 1 1 d .
H11A H 0.0782 0.7744 -0.2597 0.036 Uiso 1 1 calc R
H11B H 0.1690 0.8964 -0.2784 0.036 Uiso 1 1 calc R
H11C H -0.0273 0.8896 -0.2344 0.036 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
O3 0.0231(13) 0.0134(13) 0.0223(14) -0.0014(7) 0.0015(9) 0.0001(7)
O2 0.0352(14) 0.0259(14) 0.0343(14) -0.0124(10) -0.0080(10) 0.0038(9)
N1 0.0285(15) 0.0153(15) 0.0296(16) -0.0001(10) 0.0053(11) -0.0012(9)
O1 0.084(2) 0.0156(15) 0.0361(16) 0.0044(10) 0.0042(14) 0.0011(11)
C1 0.0164(14) 0.0189(16) 0.0188(16) -0.0002(10) 0.0037(11) 0.0006(10)
C3 0.0173(15) 0.0163(18) 0.0213(17) 0.0024(10) 0.0046(12) -0.0001(10)
C10 0.0198(16) 0.0173(16) 0.0211(17) -0.0016(11) 0.0030(12) -0.0029(10)
C6 0.0199(15) 0.0217(16) 0.0219(16) -0.0040(11) 0.0042(12) -0.0010(10)
C7 0.0162(15) 0.0242(17) 0.0205(16) 0.0000(10) 0.0019(11) 0.0016(10)
C2 0.0182(15) 0.0178(16) 0.0186(15) 0.0022(10) 0.0048(11) 0.0003(10)
C9 0.0130(15) 0.0193(17) 0.0233(17) -0.0011(11) 0.0047(11) 0.0006(10)
C5 0.0221(16) 0.0169(16) 0.0297(18) -0.0032(12) 0.0062(13) 0.0002(10)
C8 0.0186(15) 0.0134(15) 0.0254(16) -0.0007(11) 0.0065(11) -0.0013(10)
C4 0.0243(16) 0.0149(16) 0.0262(17) 0.0001(12) 0.0059(12) -0.0006(10)
C11 0.0247(17) 0.0231(17) 0.0232(18) -0.0025(11) 0.0011(13) 0.0007(11)
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
C8 O3 C1 105.6(2)
O1 N1 O2 122.8(3)
O1 N1 C10 116.3(3)
O2 N1 C10 120.9(3)
C2 C1 O3 111.0(2)
C2 C1 C9 132.0(3)
O3 C1 C9 117.0(2)
C8 C3 C4 118.7(3)
C8 C3 C2 105.8(2)
C4 C3 C2 135.5(3)
C9 C10 N1 125.1(3)
C7 C6 C5 121.9(3)
C6 C7 C8 115.2(3)
C1 C2 C3 107.4(2)
C10 C9 C1 116.7(3)
C10 C9 C11 126.8(3)
C1 C9 C11 116.5(2)
C4 C5 C6 121.8(3)
O3 C8 C7 125.2(3)
O3 C8 C3 110.2(2)
C7 C8 C3 124.6(3)
C5 C4 C3 117.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C8 1.379(3)
O3 C1 1.388(4)
O2 N1 1.228(4)
N1 O1 1.231(3)
N1 C10 1.437(4)
C1 C2 1.356(4)
C1 C9 1.450(4)
C3 C8 1.396(4)
C3 C4 1.411(4)
C3 C2 1.419(4)
C10 C9 1.339(4)
C6 C7 1.389(4)
C6 C5 1.405(4)
C7 C8 1.389(4)
C9 C11 1.504(4)
C5 C4 1.373(4)
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
C8 O3 C1 C2 0.1(3)
C8 O3 C1 C9 -179.6(2)
O1 N1 C10 C9 -173.9(3)
O2 N1 C10 C9 7.1(5)
C5 C6 C7 C8 -1.6(4)
O3 C1 C2 C3 0.7(3)
C9 C1 C2 C3 -179.7(3)
C8 C3 C2 C1 -1.2(3)
C4 C3 C2 C1 -180.0(3)
N1 C10 C9 C1 -179.9(2)
N1 C10 C9 C11 0.5(5)
C2 C1 C9 C10 -178.4(3)
O3 C1 C9 C10 1.2(4)
C2 C1 C9 C11 1.2(4)
O3 C1 C9 C11 -179.18(19)
C7 C6 C5 C4 2.0(4)
C1 O3 C8 C7 179.8(2)
C1 O3 C8 C3 -0.9(3)
C6 C7 C8 O3 -180.0(2)
C6 C7 C8 C3 0.8(4)
C4 C3 C8 O3 -179.7(2)
C2 C3 C8 O3 1.3(3)
C4 C3 C8 C7 -0.3(4)
C2 C3 C8 C7 -179.3(2)
C6 C5 C4 C3 -1.5(4)
C8 C3 C4 C5 0.6(4)
C2 C3 C4 C5 179.3(3)
