#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:04:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180464 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213376.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213376
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Sun, Hsu-I'
'Shr, Yeong-Jou'
'Lin, Kuan-Jiuh'
_publ_section_title
;
 A novel oxidative alkylation--nitration of 1,3-dicarbonyl compounds to
 dicyclopentadiene and norbornene †
;
_journal_issue                   17
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2939
_journal_paper_doi               10.1039/b004095i
_journal_year                    2000
_chemical_formula_sum            'C15 H19 N O5'
_chemical_formula_weight         293.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.637(4)
_cell_length_b                   17.757(7)
_cell_length_c                   9.976(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.56
_cell_measurement_theta_min      8.86
_cell_volume                     1436.3(14)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2697
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        2.5
_diffrn_standards_interval_count 300
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9051
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0112(25)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.043
_refine_ls_goodness_of_fit_obs   1.192
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_restrained_S_obs      1.192
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_obs          0.0427
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0577P)²+0.1441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1222
_refine_ls_wR_factor_obs         0.1092
_reflns_number_observed          1639
_reflns_number_total             2523
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b004095isup1.cif
_cod_data_source_block           1546
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'MONOCLNIC' was replaced with
'monoclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.1441P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.1441P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1436.4(13)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7213376
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
O1 O 0.3933(3) 0.70045(11) -0.1998(2) 0.0791(7) Uani 1 d
O2 O 0.6567(2) 0.86264(14) -0.1018(2) 0.0817(7) Uani 1 d
O3 O 0.3535(2) 0.94774(8) 0.09579(14) 0.0402(4) Uani 1 d
O4 O 0.1660(3) 0.97418(12) 0.1963(2) 0.0691(6) Uani 1 d
O5 O 0.4282(3) 0.98076(11) 0.3177(2) 0.0655(6) Uani 1 d
C1 C 0.0310(3) 0.87273(13) -0.3089(2) 0.0421(6) Uani 1 d
C2 C 0.1415(3) 0.94426(13) -0.2961(2) 0.0381(5) Uani 1 d
C3 C 0.1867(4) 0.9442(2) -0.4301(3) 0.0503(7) Uani 1 d
C4 C 0.1104(3) 0.8815(2) -0.5137(3) 0.0521(7) Uani 1 d
C5 C 0.0206(4) 0.8380(2) -0.4514(3) 0.0539(7) Uani 1 d
C6 C 0.2855(3) 0.93059(12) -0.1553(2) 0.0329(5) Uani 1 d
C7 C 0.2126(3) 0.94057(13) -0.0375(2) 0.0367(5) Uani 1 d
C8 C 0.1115(3) 0.86826(14) -0.0453(3) 0.0417(6) Uani 1 d
C9 C 0.1286(3) 0.82760(13) -0.1750(2) 0.0390(5) Uani 1 d
C10 C 0.3077(2) 0.84499(12) -0.1621(2) 0.0332(5) Uani 1 d
C11 C 0.5555(5) 0.6711(2) 0.0360(4) 0.0601(8) Uani 1 d
C12 C 0.4584(3) 0.72280(13) -0.0793(2) 0.0419(6) Uani 1 d
C13 C 0.4413(3) 0.80528(12) -0.0406(2) 0.0358(5) Uani 1 d
C14 C 0.6112(3) 0.84215(14) -0.0071(3) 0.0469(6) Uani 1 d
C15 C 0.7149(5) 0.8523(2) 0.1462(4) 0.0705(9) Uani 1 d
N1 N 0.3107(3) 0.96948(11) 0.2125(2) 0.0479(5) Uani 1 d
H7 H 0.1501(25) 0.9853(12) -0.0448(20) 0.031(5) Uiso 1 d
H2 H 0.0877(24) 0.9866(12) -0.2880(20) 0.025(5) Uiso 1 d
H10 H 0.3222(23) 0.8315(11) -0.2482(22) 0.033(5) Uiso 1 d
H8B H -0.0030(31) 0.8796(13) -0.0587(23) 0.046(6) Uiso 1 d
H13 H 0.4180(23) 0.8032(11) 0.0445(21) 0.028(5) Uiso 1 d
H9 H 0.0974(28) 0.7745(15) -0.1798(23) 0.051(7) Uiso 1 d
H6 H 0.3823(28) 0.9622(13) -0.1418(23) 0.039(6) Uiso 1 d
H1 H -0.0727(28) 0.8847(13) -0.3033(22) 0.043(6) Uiso 1 d
H8A H 0.1546(26) 0.8396(12) 0.0367(23) 0.036(6) Uiso 1 d
H4 H 0.1231(29) 0.8684(14) -0.6030(27) 0.057(7) Uiso 1 d
H11C H 0.6663(56) 0.6848(23) 0.0674(41) 0.126(16) Uiso 1 d
H5 H -0.0389(45) 0.8035(21) -0.4837(38) 0.106(14) Uiso 1 d
H15B H 0.7149(41) 0.8045(22) 0.1941(34) 0.094(11) Uiso 1 d
H15A H 0.8218(47) 0.8675(19) 0.1513(34) 0.094(12) Uiso 1 d
H11A H 0.5478(41) 0.6271(21) 0.0123(36) 0.092(12) Uiso 1 d
H15C H 0.6675(51) 0.8921(27) 0.1902(45) 0.143(17) Uiso 1 d
H11B H 0.5317(45) 0.6776(21) 0.1180(41) 0.111(14) Uiso 1 d
H3A H 0.3078(57) 0.9427(23) -0.4088(42) 0.136(15) Uiso 1 d
H3B H 0.1820(46) 0.9909(22) -0.4699(39) 0.110(13) Uiso 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 O3 C7 113.9(2)
C5 C1 C9 116.0(2)
C5 C1 C2 104.1(2)
C9 C1 C2 102.4(2)
C5 C1 H1 113.3(13)
C9 C1 H1 108.3(14)
C2 C1 H1 112.1(14)
C3 C2 C6 115.5(2)
C3 C2 C1 105.2(2)
C6 C2 C1 103.0(2)
C3 C2 H2 112.1(12)
C6 C2 H2 109.2(12)
C1 C2 H2 111.4(13)
C4 C3 C2 108.2(2)
C4 C3 H3A 110.4(24)
C2 C3 H3A 112.5(23)
C4 C3 H3B 121.1(23)
C2 C3 H3B 113.3(24)
H3A C3 H3B 90.2(31)
C5 C4 C3 113.3(2)
C5 C4 H4 122.6(15)
C3 C4 H4 124.1(15)
C4 C5 C1 109.3(3)
C4 C5 H5 129.4(28)
C1 C5 H5 120.9(28)
C7 C6 C10 103.9(2)
C7 C6 C2 105.5(2)
C10 C6 C2 100.9(2)
C7 C6 H6 112.9(13)
C10 C6 H6 117.4(13)
C2 C6 H6 114.8(13)
O3 C7 C6 106.0(2)
O3 C7 C8 113.4(2)
C6 C7 C8 104.0(2)
O3 C7 H7 105.7(12)
C6 C7 H7 114.4(12)
C8 C7 H7 113.3(12)
C9 C8 C7 102.6(2)
C9 C8 H8B 111.8(13)
C7 C8 H8B 111.5(14)
C9 C8 H8A 111.1(13)
C7 C8 H8A 111.4(13)
H8B C8 H8A 108.4(19)
C8 C9 C1 107.7(2)
C8 C9 C10 102.8(2)
C1 C9 C10 101.7(2)
C8 C9 H9 113.0(13)
C1 C9 H9 113.7(13)
C10 C9 H9 116.7(14)
C13 C10 C6 119.6(2)
C13 C10 C9 115.9(2)
C6 C10 C9 93.7(2)
C13 C10 H10 107.8(12)
C6 C10 H10 110.5(12)
C9 C10 H10 108.6(12)
C12 C11 H11C 109.9(24)
C12 C11 H11A 113.7(24)
H11C C11 H11A 108.7(33)
C12 C11 H11B 111.9(23)
H11C C11 H11B 100.8(31)
H11A C11 H11B 111.1(32)
O1 C12 C11 120.9(2)
O1 C12 C13 120.9(2)
C11 C12 C13 118.2(2)
C10 C13 C12 110.7(2)
C10 C13 C14 112.3(2)
C12 C13 C14 107.1(2)
C10 C13 H13 113.4(12)
C12 C13 H13 105.1(12)
C14 C13 H13 107.9(12)
O2 C14 C15 121.8(3)
O2 C14 C13 120.4(2)
C15 C14 C13 117.7(3)
C14 C15 H15B 107.2(19)
C14 C15 H15A 108.6(20)
H15B C15 H15A 112.8(29)
C14 C15 H15C 110.2(23)
H15B C15 H15C 109.5(33)
H15A C15 H15C 108.5(31)
O5 N1 O4 129.1(2)
O5 N1 O3 112.9(2)
O4 N1 O3 117.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.205(3)
O2 C14 1.198(3)
O3 N1 1.392(2)
O3 C7 1.466(3)
O4 N1 1.207(3)
O5 N1 1.198(3)
C1 C5 1.524(3)
C1 C9 1.537(3)
C1 C2 1.567(3)
C1 H1 0.94(2)
C2 C3 1.516(3)
C2 C6 1.541(3)
C2 H2 0.90(2)
C3 C4 1.410(4)
C3 H3A 0.99(5)
C3 H3B 0.92(4)
C4 C5 1.385(4)
C4 H4 0.96(3)
C5 H5 0.79(4)
C6 C7 1.523(3)
C6 C10 1.537(3)
C6 H6 0.98(2)
C7 C8 1.540(3)
C7 H7 0.95(2)
C8 C9 1.533(3)
C8 H8B 0.97(2)
C8 H8A 0.93(2)
C9 C10 1.538(3)
C9 H9 0.98(3)
C10 C13 1.528(3)
C10 H10 0.94(2)
C11 C12 1.485(4)
C11 H11C 0.93(5)
C11 H11A 0.81(4)
C11 H11B 0.92(4)
C12 C13 1.535(3)
C13 C14 1.535(3)
C13 H13 0.94(2)
C14 C15 1.494(4)
C15 H15B 0.97(4)
C15 H15A 0.95(4)
C15 H15C 0.99(5)
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
C5 C1 C2 C3 -0.7(2)
C9 C1 C2 C3 120.5(2)
C5 C1 C2 C6 -122.0(2)
C9 C1 C2 C6 -0.9(2)
C6 C2 C3 C4 113.8(2)
C1 C2 C3 C4 1.0(3)
C2 C3 C4 C5 -1.1(3)
C3 C4 C5 C1 0.6(3)
C9 C1 C5 C4 -111.6(2)
C2 C1 C5 C4 0.1(3)
C3 C2 C6 C7 174.9(2)
C1 C2 C6 C7 -71.1(2)
C3 C2 C6 C10 -77.3(2)
C1 C2 C6 C10 36.8(2)
N1 O3 C7 C6 170.1(2)
N1 O3 C7 C8 -76.4(2)
C10 C6 C7 O3 88.9(2)
C2 C6 C7 O3 -165.4(2)
C10 C6 C7 C8 -30.9(2)
C2 C6 C7 C8 74.8(2)
O3 C7 C8 C9 -118.6(2)
C6 C7 C8 C9 -3.9(2)
C7 C8 C9 C1 -69.5(2)
C7 C8 C9 C10 37.4(2)
C5 C1 C9 C8 -175.1(2)
C2 C1 C9 C8 72.3(2)
C5 C1 C9 C10 77.2(3)
C2 C1 C9 C10 -35.4(2)
C7 C6 C10 C13 -70.9(2)
C2 C6 C10 C13 -180.0(2)
C7 C6 C10 C9 51.9(2)
C2 C6 C10 C9 -57.3(2)
C8 C9 C10 C13 71.2(2)
C1 C9 C10 C13 -177.3(2)
C8 C9 C10 C6 -54.3(2)
C1 C9 C10 C6 57.1(2)
C6 C10 C13 C12 -171.7(2)
C9 C10 C13 C12 77.2(2)
C6 C10 C13 C14 -52.1(3)
C9 C10 C13 C14 -163.1(2)
O1 C12 C13 C10 12.1(3)
C11 C12 C13 C10 -167.1(2)
O1 C12 C13 C14 -110.6(3)
C11 C12 C13 C14 70.1(3)
C10 C13 C14 O2 -41.7(3)
C12 C13 C14 O2 80.0(3)
C10 C13 C14 C15 137.4(3)
C12 C13 C14 C15 -100.9(3)
C7 O3 N1 O5 -174.5(2)
C7 O3 N1 O4 5.8(3)
