#------------------------------------------------------------------------------
#$Date: 2016-02-05 03:24:14 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176198 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/47/7154770.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_7154770
loop_
_publ_author_name
'Burugupalli, Satvika'
'Shah, Sayali'
'van der Peet, Phillip L.'
'Arora, Seep'
'White, Jonathan M.'
'Williams, Spencer J.'
_publ_section_title
;
 Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as
 a selective benzoylating reagent.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              97
_journal_page_last               104
_journal_paper_doi               10.1039/c5ob02092a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27
_chemical_name_common            Benzoyl-tButylOxyma
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-06-11 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.90200(10)
_cell_length_b                   21.5230(3)
_cell_length_c                   11.2041(2)
_cell_measurement_reflns_used    4743
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      76.5290
_cell_measurement_theta_min      4.0420
_cell_volume                     1391.76(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130.0(1)
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9619
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.984
_diffrn_reflns_theta_min         4.108
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       rod
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.4756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2605
_reflns_number_total             2897
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob02092a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7154769--7154770.cif.'
_cod_database_code               7154770
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_usercomment     'Satvika Burungpalli/SJW'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C -0.1042(2) 0.40798(6) 0.61226(11) 0.0250(3) Uani 1 1 d . .
C2 C 0.0546(2) 0.35677(5) 0.58786(10) 0.0222(2) Uani 1 1 d . .
C3 C -0.0225(2) 0.32200(6) 0.47602(11) 0.0251(3) Uani 1 1 d . .
C4 C 0.5786(2) 0.28516(5) 0.68866(10) 0.0216(2) Uani 1 1 d . .
C5 C 0.6803(2) 0.23197(5) 0.63434(10) 0.0215(2) Uani 1 1 d . .
C6 C 0.5669(2) 0.20360(6) 0.52577(11) 0.0241(3) Uani 1 1 d . .
H6 H 0.4171 0.2154 0.4888 0.029 Uiso 1 1 calc R U
C7 C 0.6799(2) 0.15771(6) 0.47383(11) 0.0280(3) Uani 1 1 d . .
H7 H 0.6063 0.1389 0.4013 0.034 Uiso 1 1 calc R U
C8 C 0.9029(2) 0.13966(6) 0.52990(12) 0.0307(3) Uani 1 1 d . .
H8 H 0.9785 0.1092 0.4942 0.037 Uiso 1 1 calc R U
C9 C 1.0132(2) 0.16686(6) 0.63873(13) 0.0307(3) Uani 1 1 d . .
H9 H 1.1614 0.1541 0.6765 0.037 Uiso 1 1 calc R U
C10 C 0.9028(2) 0.21313(6) 0.69128(11) 0.0259(3) Uani 1 1 d . .
H10 H 0.9769 0.2315 0.7642 0.031 Uiso 1 1 calc R U
C11 C -0.1230(2) 0.49807(6) 0.74284(12) 0.0288(3) Uani 1 1 d . .
C12 C -0.1849(4) 0.54331(8) 0.63789(18) 0.0592(5) Uani 1 1 d . .
H12A H -0.2633 0.5785 0.6630 0.089 Uiso 1 1 calc R U
H12B H -0.0461 0.5569 0.6138 0.089 Uiso 1 1 calc R U
H12C H -0.2846 0.5232 0.5702 0.089 Uiso 1 1 calc R U
C13 C -0.3271(3) 0.47565(8) 0.79249(18) 0.0487(4) Uani 1 1 d . .
H13A H -0.4060 0.5106 0.8180 0.073 Uiso 1 1 calc R U
H13B H -0.4316 0.4532 0.7301 0.073 Uiso 1 1 calc R U
H13C H -0.2736 0.4488 0.8610 0.073 Uiso 1 1 calc R U
C14 C 0.0631(3) 0.52502(7) 0.84318(16) 0.0448(4) Uani 1 1 d . .
H14A H 0.0040 0.5612 0.8764 0.067 Uiso 1 1 calc R U
H14B H 0.1081 0.4946 0.9064 0.067 Uiso 1 1 calc R U
H14C H 0.1951 0.5363 0.8103 0.067 Uiso 1 1 calc R U
N1 N -0.0777(2) 0.29623(6) 0.38535(10) 0.0330(3) Uani 1 1 d . .
N2 N 0.24688(18) 0.34640(5) 0.66298(9) 0.0231(2) Uani 1 1 d . .
O1 O -0.29647(18) 0.41224(5) 0.55062(9) 0.0394(3) Uani 1 1 d . .
O2 O -0.00125(15) 0.44340(4) 0.70334(8) 0.0257(2) Uani 1 1 d . .
O3 O 0.35481(14) 0.29588(4) 0.62116(8) 0.0237(2) Uani 1 1 d . .
O4 O 0.66986(16) 0.31684(4) 0.77230(8) 0.0281(2) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 C1 O2 128.93(12)
O1 C1 C2 119.94(11)
O2 C1 C2 111.13(10)
N2 C2 C3 123.52(11)
N2 C2 C1 120.39(11)
C3 C2 C1 116.08(10)
N1 C3 C2 177.03(14)
O4 C4 O3 123.46(11)
O4 C4 C5 127.57(11)
O3 C4 C5 108.88(9)
C10 C5 C6 120.26(11)
C10 C5 C4 117.41(11)
C6 C5 C4 122.21(11)
C7 C6 C5 119.40(11)
C7 C6 H6 120.3
C5 C6 H6 120.3
C6 C7 C8 120.18(12)
C6 C7 H7 119.9
C8 C7 H7 119.9
C9 C8 C7 120.37(12)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 120.06(12)
C8 C9 H9 120.0
C10 C9 H9 120.0
C9 C10 C5 119.71(12)
C9 C10 H10 120.1
C5 C10 H10 120.1
O2 C11 C13 109.17(10)
O2 C11 C12 109.26(11)
C13 C11 C12 114.31(15)
O2 C11 C14 101.69(10)
C13 C11 C14 111.12(13)
C12 C11 C14 110.53(14)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C2 N2 O3 108.64(10)
C1 O2 C11 120.90(10)
N2 O3 C4 113.25(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2024(17)
C1 O2 1.3161(15)
C1 C2 1.5082(16)
C2 N2 1.2833(16)
C2 C3 1.4487(17)
C3 N1 1.1434(17)
C4 O4 1.1924(15)
C4 O3 1.3971(14)
C4 C5 1.4811(16)
C5 C10 1.3952(17)
C5 C6 1.4000(16)
C6 C7 1.3862(18)
C6 H6 0.9300
C7 C8 1.3902(19)
C7 H7 0.9300
C8 C9 1.3861(19)
C8 H8 0.9300
C9 C10 1.3868(18)
C9 H9 0.9300
C10 H10 0.9300
C11 O2 1.4932(14)
C11 C13 1.5076(19)
C11 C12 1.511(2)
C11 C14 1.513(2)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N2 O3 1.3902(13)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12C O1 0.96 2.40 3.013(2) 121.4
C13 H13B O1 0.96 2.48 3.0730(19) 120.2
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
O1 C1 C2 N2 -170.22(12)
O2 C1 C2 N2 10.31(16)
O1 C1 C2 C3 10.63(18)
O2 C1 C2 C3 -168.83(10)
O4 C4 C5 C10 4.90(19)
O3 C4 C5 C10 -178.50(10)
O4 C4 C5 C6 -171.04(12)
O3 C4 C5 C6 5.55(15)
C10 C5 C6 C7 -1.57(18)
C4 C5 C6 C7 174.26(11)
C5 C6 C7 C8 0.65(19)
C6 C7 C8 C9 0.7(2)
C7 C8 C9 C10 -1.1(2)
C8 C9 C10 C5 0.2(2)
C6 C5 C10 C9 1.14(18)
C4 C5 C10 C9 -174.89(11)
C3 C2 N2 O3 -2.88(16)
C1 C2 N2 O3 178.04(10)
O1 C1 O2 C11 -0.6(2)
C2 C1 O2 C11 178.84(10)
C13 C11 O2 C1 64.99(16)
C12 C11 O2 C1 -60.68(16)
C14 C11 O2 C1 -177.54(12)
C2 N2 O3 C4 172.89(10)
O4 C4 O3 N2 -1.37(16)
C5 C4 O3 N2 -178.14(9)
