#------------------------------------------------------------------------------
#$Date: 2015-12-17 10:22:50 +0200 (Thu, 17 Dec 2015) $
#$Revision: 171577 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/35/7223500.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_7223500
loop_
_publ_author_name
'Das, Asish R.'
'Mukherjee, Prasun'
_publ_section_title
;
 Facile synthesis of functionalized
 6-cyano-2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl acetates : a catalyst
 free approach to access the pyran fused 2-acetoxy-NH-aziridines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA24510A
_journal_year                    2015
_chemical_formula_moiety         'C18 H16 N2 O5'
_chemical_formula_sum            'C18 H16 N2 O5'
_chemical_formula_weight         340.33
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-01 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                76.794(10)
_cell_angle_beta                 72.910(9)
_cell_angle_gamma                79.128(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1462(19)
_cell_length_b                   9.013(2)
_cell_length_c                   12.122(3)
_cell_measurement_temperature    296(2)
_cell_volume                     821.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.03'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8736
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.102
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       granular
_exptl_crystal_F_000             358
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.677
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.677
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0452
_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)+(0.1993P)²+0.2536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1725
_reflns_number_gt                2741
_reflns_number_total             3181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra24510a2.cif
_cod_data_source_block           isohc_0m
_cod_original_cell_volume        821.2(3)
_cod_database_code               7223500
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_refinement_flags
O3 O 0.57652(17) 0.78420(16) 0.47796(12) 0.0635(4) Uani 1 1 d .
O2 O 0.84220(13) 0.76234(13) 0.35503(10) 0.0440(3) Uani 1 1 d .
O1 O 0.67190(14) 0.81035(12) 0.22967(10) 0.0426(3) Uani 1 1 d .
O4 O 0.22415(13) 0.72891(12) 0.17712(10) 0.0431(3) Uani 1 1 d .
O5 O 0.26490(14) 0.48354(13) 0.24892(11) 0.0499(3) Uani 1 1 d .
C5 C 0.52687(17) 0.77107(16) 0.21598(12) 0.0328(3) Uani 1 1 d .
C6 C 0.41657(18) 0.90294(16) 0.17172(12) 0.0354(3) Uani 1 1 d .
C13 C 0.7237(2) 0.80507(18) 0.45388(15) 0.0477(4) Uani 1 1 d .
C1 C 0.77618(17) 0.69670(17) 0.28686(13) 0.0378(3) Uani 1 1 d .
C9 C 0.4532(2) 1.05418(17) 0.14622(14) 0.0464(4) Uani 1 1 d .
H3 H 0.5528 1.0754 0.1591 0.056 Uiso 1 1 calc R
C10 C 0.3421(3) 1.1720(2) 0.10209(17) 0.0571(5) Uani 1 1 d .
H4 H 0.3661 1.2727 0.0861 0.069 Uiso 1 1 calc R
C11 C 0.1946(2) 1.1410(2) 0.08133(17) 0.0587(5) Uani 1 1 d .
H5 H 0.1213 1.2211 0.0502 0.070 Uiso 1 1 calc R
C7 C 0.26719(18) 0.87487(17) 0.15235(13) 0.0383(4) Uani 1 1 d .
C8 C 0.32341(17) 0.60399(16) 0.22479(13) 0.0363(3) Uani 1 1 d .
C4 C 0.48683(16) 0.62666(15) 0.23968(12) 0.0324(3) Uani 1 1 d .
C3 C 0.59254(16) 0.48582(15) 0.29076(12) 0.0337(3) Uani 1 1 d .
H9 H 0.5167 0.4431 0.3660 0.040 Uiso 1 1 calc R
C15 C 0.64822(19) 0.35539(17) 0.21758(14) 0.0427(4) Uani 1 1 d .
H10 H 0.5424 0.3139 0.2237 0.051 Uiso 1 1 calc R
C17 C 0.7655(2) 0.2238(2) 0.27089(18) 0.0572(5) Uani 1 1 d .
H11A H 0.7851 0.1388 0.2311 0.086 Uiso 1 1 calc R
H11B H 0.7110 0.1920 0.3527 0.086 Uiso 1 1 calc R
H11C H 0.8742 0.2575 0.2625 0.086 Uiso 1 1 calc R
C16 C 0.7280(3) 0.4081(2) 0.08750(16) 0.0591(5) Uani 1 1 d .
H12A H 0.8316 0.4515 0.0772 0.089 Uiso 1 1 calc R
H12B H 0.6470 0.4843 0.0549 0.089 Uiso 1 1 calc R
H12C H 0.7558 0.3218 0.0482 0.089 Uiso 1 1 calc R
C2 C 0.74151(17) 0.53470(16) 0.32035(12) 0.0359(3) Uani 1 1 d .
C14 C 0.8067(3) 0.8727(2) 0.52150(19) 0.0699(6) Uani 1 1 d .
H14A H 0.7301 0.9583 0.5505 0.105 Uiso 1 1 calc R
H14B H 0.9130 0.9071 0.4713 0.105 Uiso 1 1 calc R
H14C H 0.8306 0.7965 0.5864 0.105 Uiso 1 1 calc R
N1 N 0.88816(16) 0.59130(16) 0.22007(12) 0.0433(3) Uani 1 1 d .
C18 C 0.78312(19) 0.44867(18) 0.42779(14) 0.0448(4) Uani 1 1 d .
N2 N 0.8143(2) 0.3798(2) 0.51203(14) 0.0667(5) Uani 1 1 d .
C12 C 0.1557(2) 0.9923(2) 0.10650(16) 0.0534(4) Uani 1 1 d .
H18 H 0.0566 0.9713 0.0929 0.064 Uiso 1 1 calc R
H H 0.986(3) 0.567(3) 0.2402(19) 0.065(6) 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
C13 O2 C1 115.34(12)
C5 O1 C1 117.78(11)
C7 O4 C8 122.30(11)
C4 C5 O1 125.05(12)
C4 C5 C6 122.45(13)
O1 C5 C6 112.50(12)
C7 C6 C9 118.74(14)
C7 C6 C5 117.03(13)
C9 C6 C5 124.22(14)
O3 C13 O2 121.22(15)
O3 C13 C14 127.40(18)
O2 C13 C14 111.36(15)
O2 C1 O1 109.02(12)
O2 C1 N1 118.44(12)
O1 C1 N1 116.67(13)
O2 C1 C2 121.86(12)
O1 C1 C2 121.37(11)
N1 C1 C2 62.63(10)
C10 C9 C6 120.06(16)
C10 C9 H3 120.0
C6 C9 H3 120.0
C9 C10 C11 120.28(17)
C9 C10 H4 119.9
C11 C10 H4 119.9
C12 C11 C10 120.49(15)
C12 C11 H5 119.8
C10 C11 H5 119.8
O4 C7 C6 121.09(13)
O4 C7 C12 117.25(14)
C6 C7 C12 121.66(15)
O5 C8 O4 115.37(12)
O5 C8 C4 126.23(13)
O4 C8 C4 118.39(12)
C5 C4 C8 118.47(12)
C5 C4 C3 124.83(12)
C8 C4 C3 116.50(11)
C4 C3 C2 109.25(11)
C4 C3 C15 114.79(12)
C2 C3 C15 114.21(11)
C4 C3 H9 105.9
C2 C3 H9 105.9
C15 C3 H9 105.9
C16 C15 C17 111.37(14)
C16 C15 C3 114.52(13)
C17 C15 C3 110.92(13)
C16 C15 H10 106.5
C17 C15 H10 106.5
C3 C15 H10 106.5
C15 C17 H11A 109.5
C15 C17 H11B 109.5
H11A C17 H11B 109.5
C15 C17 H11C 109.5
H11A C17 H11C 109.5
H11B C17 H11C 109.5
C15 C16 H12A 109.5
C15 C16 H12B 109.5
H12A C16 H12B 109.5
C15 C16 H12C 109.5
H12A C16 H12C 109.5
H12B C16 H12C 109.5
C18 C2 C1 115.87(12)
C18 C2 N1 117.63(12)
C1 C2 N1 56.27(9)
C18 C2 C3 115.54(12)
C1 C2 C3 120.96(11)
N1 C2 C3 117.73(12)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C1 N1 C2 61.09(10)
C1 N1 H 109.9(15)
C2 N1 H 110.5(14)
N2 C18 C2 179.05(19)
C11 C12 C7 118.75(17)
C11 C12 H18 120.6
C7 C12 H18 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C13 1.189(2)
O2 C13 1.381(2)
O2 C1 1.3880(17)
O1 C5 1.3596(16)
O1 C1 1.3946(17)
O4 C7 1.3695(19)
O4 C8 1.3746(17)
O5 C8 1.2081(18)
C5 C4 1.348(2)
C5 C6 1.4481(19)
C6 C7 1.382(2)
C6 C9 1.396(2)
C13 C14 1.487(2)
C1 N1 1.407(2)
C1 C2 1.481(2)
C9 C10 1.377(2)
C9 H3 0.9300
C10 C11 1.386(3)
C10 H4 0.9300
C11 C12 1.381(3)
C11 H5 0.9300
C7 C12 1.385(2)
C8 C4 1.4517(18)
C4 C3 1.5094(18)
C3 C2 1.5249(18)
C3 C15 1.5536(19)
C3 H9 0.9800
C15 C16 1.519(3)
C15 C17 1.524(2)
C15 H10 0.9800
C17 H11A 0.9600
C17 H11B 0.9600
C17 H11C 0.9600
C16 H12A 0.9600
C16 H12B 0.9600
C16 H12C 0.9600
C2 C18 1.453(2)
C2 N1 1.5027(19)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N1 H 0.87(2)
C18 N2 1.138(2)
C12 H18 0.9300
