#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502252.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_1502252
loop_
_publ_author_name
'Chaiyaveij, Duangduan'
'Cleary, Leah'
'Batsanov, Andrei S.'
'Marder, Todd B.'
'Shea, Kenneth J.'
'Whiting, Andrew'
_publ_section_title
;
 Copper(II)-catalyzed room temperature aerobic oxidation of hydroxamic
 acids and hydrazides to acyl-nitroso and azo intermediates, and their
 Diels-Alder trapping.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3442
_journal_page_last               3445
_journal_paper_doi               10.1021/ol201188d
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_melting_point          350(1)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                65.453(6)
_cell_angle_beta                 88.454(6)
_cell_angle_gamma                84.712(7)
_cell_formula_units_Z            2
_cell_length_a                   6.0126(3)
_cell_length_b                   10.4102(5)
_cell_length_c                   10.6716(5)
_cell_measurement_reflns_used    7443
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.16
_cell_volume                     604.96(6)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement
'A short history of SHELX (Sheldrick, 2008)/Bruker'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2008)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.098254
_diffrn_orient_matrix_UB_12      0.046873
_diffrn_orient_matrix_UB_13      -0.083819
_diffrn_orient_matrix_UB_21      0.056942
_diffrn_orient_matrix_UB_22      -0.074345
_diffrn_orient_matrix_UB_23      -0.032186
_diffrn_orient_matrix_UB_31      -0.122327
_diffrn_orient_matrix_UB_32      -0.059347
_diffrn_orient_matrix_UB_33      0.050608
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_refln_scan_width         0.3
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11016
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.10
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0407
_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)+(0.0628P)²+0.1250P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                3209
_reflns_number_total             3525
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol201188d_si_001.cif
_cod_data_source_block           4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        604.96(5)
_cod_database_code               1502252
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.35900(11) 0.41548(6) 0.27060(7) 0.02122(15) Uani 1 1 d
O2 O 0.67636(12) 0.40042(6) 0.42601(7) 0.02446(16) Uani 1 1 d
O3 O 0.39639(12) 0.18029(7) 0.32207(7) 0.02517(16) Uani 1 1 d
N N 0.65367(13) 0.27702(7) 0.40043(8) 0.02049(16) Uani 1 1 d
C1 C 0.74878(15) 0.35659(9) 0.56937(9) 0.02212(18) Uani 1 1 d
H1 H 0.749(2) 0.4457(14) 0.5776(14) 0.024(3) Uiso 1 1 d
C2 C 0.45825(14) 0.28335(9) 0.33218(9) 0.01870(17) Uani 1 1 d
C3 C 0.16081(16) 0.42638(9) 0.18932(9) 0.02274(18) Uani 1 1 d
H3b H 0.198(2) 0.3756(14) 0.1312(14) 0.028(3) Uiso 1 1 d
H3a H 0.043(2) 0.3810(14) 0.2545(15) 0.028(3) Uiso 1 1 d
C4 C 0.71600(14) 0.14294(8) 0.52317(9) 0.01997(17) Uani 1 1 d
H4 H 0.694(2) 0.0668(14) 0.4960(14) 0.026(3) Uiso 1 1 d
C5 C 0.57045(16) 0.14313(10) 0.64045(10) 0.02471(19) Uani 1 1 d
H5 H 0.469(3) 0.0746(19) 0.6823(18) 0.052(5) Uiso 1 1 d
C6 C 0.58691(17) 0.26113(11) 0.66365(11) 0.0297(2) Uani 1 1 d
H6 H 0.504(3) 0.2880(19) 0.7270(19) 0.054(5) Uiso 1 1 d
C7 C 0.97843(15) 0.27584(10) 0.58665(10) 0.02397(18) Uani 1 1 d
H7a H 1.087(3) 0.337(2) 0.532(2) 0.058(5) Uiso 1 1 d
H7b H 1.035(3) 0.2510(18) 0.6774(19) 0.051(5) Uiso 1 1 d
C8 C 0.95917(15) 0.14761(10) 0.55584(10) 0.02444(19) Uani 1 1 d
H8a H 1.050(3) 0.1465(17) 0.4806(17) 0.043(4) Uiso 1 1 d
H8b H 1.013(3) 0.0548(19) 0.6318(19) 0.051(4) Uiso 1 1 d
C9 C 0.09846(15) 0.58096(9) 0.10379(9) 0.02091(18) Uani 1 1 d
C10 C 0.24477(17) 0.66231(11) 0.00529(11) 0.0300(2) Uani 1 1 d
H10 H 0.394(3) 0.6176(16) -0.0034(16) 0.041(4) Uiso 1 1 d
C11 C 0.1839(2) 0.80462(11) -0.07677(12) 0.0345(2) Uani 1 1 d
H11 H 0.291(3) 0.8581(18) -0.1443(18) 0.050(4) Uiso 1 1 d
C12 C -0.0237(2) 0.86607(10) -0.06126(10) 0.0321(2) Uani 1 1 d
H12 H -0.069(3) 0.9667(17) -0.1191(18) 0.046(4) Uiso 1 1 d
C13 C -0.17101(19) 0.78561(11) 0.03540(11) 0.0317(2) Uani 1 1 d
H13 H -0.323(3) 0.8310(19) 0.0448(18) 0.051(4) Uiso 1 1 d
C14 C -0.10944(17) 0.64293(10) 0.11831(10) 0.02599(19) Uani 1 1 d
H14 H -0.215(2) 0.5853(16) 0.1912(16) 0.037(4) 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
C2 O1 C3 113.73(7)
N O2 C1 109.64(6)
O2 N C4 112.21(7)
C2 N O2 113.92(7)
C2 N C4 116.70(7)
O2 C1 H1 103.2(8)
O2 C1 C6 109.09(7)
O2 C1 C7 107.30(7)
C6 C1 H1 113.2(8)
C6 C1 C7 109.71(7)
C7 C1 H1 113.9(8)
O1 C2 N 112.75(7)
O3 C2 O1 124.90(8)
O3 C2 N 122.12(8)
O1 C3 H3b 108.1(8)
O1 C3 H3a 107.2(8)
O1 C3 C9 107.41(7)
H3a C3 H3b 110.1(11)
C9 C3 H3b 111.2(8)
C9 C3 H3a 112.5(8)
N C4 H4 105.9(8)
N C4 C5 107.58(7)
N C4 C8 106.14(7)
C5 C4 H4 113.9(8)
C5 C4 C8 109.87(8)
C8 C4 H4 113.0(8)
C4 C5 H5 121.8(11)
C6 C5 C4 111.79(8)
C6 C5 H5 126.0(11)
C1 C6 H6 120.2(11)
C5 C6 C1 112.48(8)
C5 C6 H6 127.2(11)
C1 C7 H7a 110.9(11)
C1 C7 H7b 109.5(11)
H7a C7 H7b 100.8(15)
C8 C7 C1 108.71(7)
C8 C7 H7a 114.0(11)
C8 C7 H7b 112.7(10)
C4 C8 H8a 109.0(10)
C4 C8 H8b 108.8(10)
C7 C8 C4 108.79(7)
C7 C8 H8a 114.0(10)
C7 C8 H8b 114.7(10)
H8a C8 H8b 101.2(14)
C10 C9 C3 120.41(8)
C14 C9 C3 120.15(8)
C14 C9 C10 119.38(8)
C9 C10 H10 118.9(9)
C11 C10 C9 120.33(10)
C11 C10 H10 120.8(9)
C10 C11 H11 117.8(10)
C12 C11 C10 119.99(10)
C12 C11 H11 122.2(10)
C11 C12 H12 120.6(10)
C13 C12 C11 120.05(9)
C13 C12 H12 119.4(10)
C12 C13 H13 119.4(10)
C12 C13 C14 119.96(10)
C14 C13 H13 120.6(10)
C9 C14 C13 120.28(9)
C9 C14 H14 119.9(9)
C13 C14 H14 119.8(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3411(10)
O1 C3 1.4609(10)
O2 N 1.4383(9)
O2 C1 1.4689(11)
O3 C2 1.2137(10)
N C2 1.3811(11)
N C4 1.4885(11)
C1 H1 0.968(13)
C1 C6 1.4972(13)
C1 C7 1.5226(13)
C3 H3b 0.979(14)
C3 H3a 0.983(14)
C3 C9 1.5001(12)
C4 H4 0.972(13)
C4 C5 1.5083(13)
C4 C8 1.5220(13)
C5 H5 0.937(18)
C5 C6 1.3625(14)
C6 H6 0.946(19)
C7 H7a 0.962(19)
C7 H7b 0.956(18)
C7 C8 1.5161(13)
C8 H8a 0.964(17)
C8 H8b 1.000(18)
C9 C10 1.3942(13)
C9 C14 1.3881(13)
C10 H10 0.993(16)
C10 C11 1.3911(14)
C11 H11 0.978(17)
C11 C12 1.3871(17)
C12 H12 0.986(16)
C12 C13 1.3856(16)
C13 H13 1.012(18)
C13 C14 1.3966(13)
C14 H14 1.012(15)
