#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:53:56 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234529 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/63/4036311.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_4036311
loop_
_publ_author_name
'Chaiyaveij, Duangduan'
'Batsanov, Andrei S.'
'Fox, Mark A.'
'Marder, Todd B.'
'Whiting, Andrew'
_publ_section_title
;
 An Experimental and Computational Approach to Understanding the Reactions
 of Acyl Nitroso Compounds in [4 + 2] Cycloadditions.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9518
_journal_page_last               9534
_journal_paper_doi               10.1021/acs.joc.5b01470
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C12 H11 N O3'
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.22
_chemical_name_systematic
;
 phenyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-03-30
_audit_creation_method
;
Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.658(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8418(5)
_cell_length_b                   8.6844(7)
_cell_length_c                   20.7247(19)
_cell_measurement_reflns_used    4717
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.977
_cell_measurement_theta_min      2.543
_cell_volume                     1050.98(16)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12722
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         1.97
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
R(int) was 0.0682 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.7769.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0493
_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)+(0.0913P)²+0.1467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1506
_reflns_number_gt                2376
_reflns_number_total             3069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo5b01470_si_002.cif
_cod_data_source_block           36
_cod_database_code               4036311
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
O1 O 0.38372(16) 0.40154(10) 0.58992(4) 0.0225(2) Uani 1 1 d .
O2 O 0.22961(16) 0.16871(10) 0.61342(4) 0.0230(2) Uani 1 1 d .
O3 O -0.00217(15) 0.17072(10) 0.50162(4) 0.0215(2) Uani 1 1 d .
N1 N 0.11693(17) 0.30798(12) 0.52232(5) 0.0183(2) Uani 1 1 d .
C1 C 0.24623(19) 0.27773(13) 0.57822(6) 0.0177(2) Uani 1 1 d .
C2 C 0.0686(2) 0.14933(14) 0.43395(6) 0.0224(3) Uani 1 1 d .
H2 H -0.0285 0.0773 0.4073 0.027 Uiso 1 1 calc R
C3 C 0.3211(2) 0.11239(16) 0.43739(6) 0.0266(3) Uani 1 1 d .
H3 H 0.3900 0.0157 0.4288 0.032 Uiso 1 1 calc R
C4 C 0.4287(2) 0.24226(16) 0.45490(6) 0.0239(3) Uani 1 1 d .
H4 H 0.5893 0.2565 0.4605 0.029 Uiso 1 1 calc R
C5 C 0.2447(2) 0.36189(14) 0.46399(6) 0.0194(2) Uani 1 1 d .
H5 H 0.2961 0.4717 0.4644 0.023 Uiso 1 1 calc R
C6 C 0.0686(2) 0.31749(14) 0.41120(6) 0.0216(3) Uani 1 1 d .
H6A H 0.1253 0.3306 0.3670 0.026 Uiso 1 1 calc R
H6B H -0.0811 0.3694 0.4156 0.026 Uiso 1 1 calc R
C7 C 0.5174(2) 0.40041(14) 0.64772(6) 0.0205(3) Uani 1 1 d .
C8 C 0.4511(2) 0.49646(16) 0.69692(7) 0.0283(3) Uani 1 1 d .
H8 H 0.3131 0.5541 0.6931 0.034 Uiso 1 1 calc R
C9 C 0.5914(3) 0.50664(19) 0.75223(7) 0.0353(4) Uani 1 1 d .
H9 H 0.5496 0.5722 0.7867 0.042 Uiso 1 1 calc R
C10 C 0.7914(3) 0.42155(18) 0.75716(7) 0.0309(3) Uani 1 1 d .
H10 H 0.8869 0.4293 0.7949 0.037 Uiso 1 1 calc R
C11 C 0.8532(2) 0.32508(16) 0.70726(7) 0.0264(3) Uani 1 1 d .
H11 H 0.9899 0.2661 0.7111 0.032 Uiso 1 1 calc R
C12 C 0.7156(2) 0.31457(14) 0.65161(6) 0.0226(3) Uani 1 1 d .
H12 H 0.7573 0.2496 0.6170 0.027 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
O1 0.0275(5) 0.0196(4) 0.0201(4) 0.0015(3) -0.0062(3) -0.0068(3)
O2 0.0267(5) 0.0204(4) 0.0216(4) 0.0037(3) -0.0038(3) -0.0046(3)
O3 0.0224(4) 0.0212(4) 0.0206(4) 0.0012(3) -0.0033(3) -0.0087(3)
N1 0.0187(5) 0.0170(5) 0.0190(5) 0.0010(4) -0.0013(4) -0.0032(3)
C1 0.0170(5) 0.0176(5) 0.0185(5) -0.0010(4) 0.0007(4) -0.0007(4)
C2 0.0293(6) 0.0201(5) 0.0178(6) 0.0000(4) -0.0028(5) -0.0051(5)
C3 0.0322(7) 0.0240(6) 0.0236(6) -0.0014(5) 0.0014(5) 0.0058(5)
C4 0.0200(5) 0.0300(6) 0.0220(6) 0.0019(5) 0.0025(4) 0.0015(5)
C5 0.0217(6) 0.0194(5) 0.0171(5) 0.0024(4) 0.0007(4) -0.0037(4)
C6 0.0231(6) 0.0217(6) 0.0199(6) 0.0032(4) -0.0038(4) -0.0022(4)
C7 0.0227(6) 0.0206(5) 0.0180(5) 0.0000(4) -0.0026(4) -0.0051(4)
C8 0.0274(7) 0.0312(7) 0.0259(7) -0.0074(5) -0.0033(5) 0.0041(5)
C9 0.0364(8) 0.0433(9) 0.0258(7) -0.0140(6) -0.0038(6) 0.0042(6)
C10 0.0319(7) 0.0385(8) 0.0219(6) -0.0022(5) -0.0075(5) -0.0008(6)
C11 0.0228(6) 0.0290(7) 0.0272(7) 0.0015(5) -0.0031(5) -0.0002(5)
C12 0.0250(6) 0.0220(6) 0.0210(6) -0.0015(4) 0.0015(5) -0.0023(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
C1 O1 C7 117.10(9)
N1 O3 C2 103.87(8)
O3 N1 C5 105.28(8)
C1 N1 O3 109.77(9)
C1 N1 C5 117.11(9)
O1 C1 N1 107.65(9)
O2 C1 O1 124.95(11)
O2 C1 N1 127.15(11)
O3 C2 H2 115.5
O3 C2 C3 106.27(10)
O3 C2 C6 100.00(10)
C3 C2 H2 115.5
C3 C2 C6 102.01(10)
C6 C2 H2 115.5
C2 C3 H3 126.7
C4 C3 C2 106.56(11)
C4 C3 H3 126.7
C3 C4 H4 126.8
C3 C4 C5 106.46(11)
C5 C4 H4 126.8
N1 C5 H5 116.3
N1 C5 C6 98.99(9)
C4 C5 N1 104.83(9)
C4 C5 H5 116.3
C4 C5 C6 101.76(10)
C6 C5 H5 116.3
C2 C6 H6A 113.4
C2 C6 H6B 113.4
C5 C6 C2 91.50(9)
C5 C6 H6A 113.4
C5 C6 H6B 113.4
H6A C6 H6B 110.7
C8 C7 O1 117.53(11)
C12 C7 O1 119.81(11)
C12 C7 C8 122.48(12)
C7 C8 H8 120.8
C7 C8 C9 118.35(13)
C9 C8 H8 120.8
C8 C9 H9 119.9
C10 C9 C8 120.17(13)
C10 C9 H9 119.9
C9 C10 H10 119.8
C9 C10 C11 120.32(13)
C11 C10 H10 119.8
C10 C11 H11 119.9
C10 C11 C12 120.12(13)
C12 C11 H11 119.9
C7 C12 C11 118.56(12)
C7 C12 H12 120.7
C11 C12 H12 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3597(14)
O1 C7 1.4110(14)
O2 C1 1.2009(15)
O3 N1 1.4394(13)
O3 C2 1.4851(15)
N1 C1 1.3897(15)
N1 C5 1.5132(15)
C2 H2 1.0000
C2 C3 1.5095(19)
C2 C6 1.5346(17)
C3 H3 0.9500
C3 C4 1.3363(19)
C4 H4 0.9500
C4 C5 1.5107(17)
C5 H5 1.0000
C5 C6 1.5295(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.3815(18)
C7 C12 1.3773(18)
C8 H8 0.9500
C8 C9 1.392(2)
C9 H9 0.9500
C9 C10 1.384(2)
C10 H10 0.9500
C10 C11 1.387(2)
C11 H11 0.9500
C11 C12 1.3897(18)
C12 H12 0.9500
