#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/33/8103328.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_8103328
loop_
_publ_author_name
'Fang Huang'
'Feng Zhang'
'Hongmei Xu'
_publ_section_title
;
 Crystal structure of
 spiro[(indane-1,3-dione)-2,3'-(2'-methyl-2'-methyloxycarbonyl-hexahydro-1'H-pyrrolizine)],
 C18H19NO4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              225
_journal_volume                  227
_journal_year                    2012
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.081(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.204(6)
_cell_length_b                   14.888(9)
_cell_length_c                   10.750(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1626.7(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0815
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12301
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 450
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0891
_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)+(0.0846P)²+1.3325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2260
_reflns_number_gt                1948
_reflns_number_total             3312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3668.cff
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8103328
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7925(3) 0.0916(2) 0.2605(3) 0.0406(8) Uani 1 1 d .
C2 C 0.7945(4) -0.0138(2) 0.2765(3) 0.0481(9) Uani 1 1 d .
C3 C 0.7264(4) -0.0432(3) 0.1508(4) 0.0639(11) Uani 1 1 d .
H3A H 0.7491 -0.1047 0.1320 0.077 Uiso 1 1 calc R
H3B H 0.6316 -0.0386 0.1507 0.077 Uiso 1 1 calc R
C4 C 0.7775(5) 0.0211(3) 0.0573(4) 0.0668(12) Uani 1 1 d .
H4A H 0.8541 -0.0052 0.0221 0.080 Uiso 1 1 calc R
C5 C 0.6812(6) 0.0578(4) -0.0485(5) 0.107(2) Uani 1 1 d .
H5A H 0.6834 0.0219 -0.1235 0.128 Uiso 1 1 calc R
H5B H 0.5920 0.0588 -0.0240 0.128 Uiso 1 1 calc R
C6 C 0.7300(6) 0.1510(4) -0.0687(5) 0.1042(19) Uani 1 1 d .
H6A H 0.6616 0.1883 -0.1104 0.125 Uiso 1 1 calc R
H6B H 0.8056 0.1506 -0.1174 0.125 Uiso 1 1 calc R
C7 C 0.7672(4) 0.1832(3) 0.0631(4) 0.0646(12) Uani 1 1 d .
H7A H 0.8339 0.2296 0.0642 0.077 Uiso 1 1 calc R
H7B H 0.6910 0.2069 0.1000 0.077 Uiso 1 1 calc R
C8 C 0.6596(3) 0.1296(2) 0.2973(3) 0.0416(8) Uani 1 1 d .
C9 C 0.6848(3) 0.1885(2) 0.4068(3) 0.0435(8) Uani 1 1 d .
C10 C 0.5955(4) 0.2312(3) 0.4758(4) 0.0618(11) Uani 1 1 d .
H10A H 0.5055 0.2264 0.4538 0.074 Uiso 1 1 calc R
C11 C 0.6429(5) 0.2816(3) 0.5789(4) 0.0699(12) Uani 1 1 d .
H11A H 0.5843 0.3104 0.6270 0.084 Uiso 1 1 calc R
C12 C 0.7776(5) 0.2890(3) 0.6105(4) 0.0670(12) Uani 1 1 d .
H12A H 0.8079 0.3228 0.6799 0.080 Uiso 1 1 calc R
C13 C 0.8670(4) 0.2471(3) 0.5412(4) 0.0564(10) Uani 1 1 d .
H13A H 0.9569 0.2527 0.5628 0.068 Uiso 1 1 calc R
C14 C 0.8200(3) 0.1964(2) 0.4383(3) 0.0426(8) Uani 1 1 d .
C15 C 0.8926(3) 0.1438(2) 0.3505(3) 0.0441(9) Uani 1 1 d .
C16 C 0.7228(4) -0.0451(3) 0.3845(4) 0.0586(11) Uani 1 1 d .
C17 C 0.9377(4) -0.0513(3) 0.2948(4) 0.0694(12) Uani 1 1 d .
H17A H 0.9350 -0.1154 0.3042 0.104 Uiso 1 1 calc R
H17B H 0.9827 -0.0251 0.3682 0.104 Uiso 1 1 calc R
H17C H 0.9835 -0.0364 0.2233 0.104 Uiso 1 1 calc R
C18 C 0.7022(5) -0.0262(4) 0.6020(4) 0.0936(17) Uani 1 1 d .
H18A H 0.7417 0.0080 0.6711 0.140 Uiso 1 1 calc R
H18B H 0.7132 -0.0891 0.6195 0.140 Uiso 1 1 calc R
H18C H 0.6101 -0.0124 0.5894 0.140 Uiso 1 1 calc R
N1 N 0.8183(3) 0.1029(2) 0.1306(3) 0.0492(8) Uani 1 1 d .
O1 O 0.5522(2) 0.11267(19) 0.2436(2) 0.0605(8) Uani 1 1 d .
O2 O 1.0118(2) 0.14374(19) 0.3460(3) 0.0635(8) Uani 1 1 d .
O3 O 0.6351(4) -0.1006(3) 0.3786(3) 0.1103(14) Uani 1 1 d .
O4 O 0.7647(3) -0.0040(2) 0.4907(3) 0.0657(8) 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 0.0033 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
N1 C1 C15 112.0(3)
N1 C1 C8 116.1(3)
C15 C1 C8 101.5(3)
N1 C1 C2 102.6(3)
C15 C1 C2 115.4(3)
C8 C1 C2 109.7(3)
C16 C2 C3 112.4(3)
C16 C2 C17 107.9(3)
C3 C2 C17 110.9(3)
C16 C2 C1 113.0(3)
C3 C2 C1 100.8(3)
C17 C2 C1 111.8(3)
C4 C3 C2 104.4(3)
N1 C4 C3 105.2(3)
N1 C4 C5 103.4(4)
C3 C4 C5 118.7(4)
C6 C5 C4 103.7(4)
C5 C6 C7 102.5(4)
N1 C7 C6 104.7(4)
O1 C8 C9 126.0(3)
O1 C8 C1 124.9(3)
C9 C8 C1 109.1(3)
C10 C9 C14 121.1(3)
C10 C9 C8 128.9(3)
C14 C9 C8 110.0(3)
C9 C10 C11 118.5(4)
C10 C11 C12 120.3(4)
C13 C12 C11 121.3(4)
C12 C13 C14 118.5(4)
C13 C14 C9 120.2(3)
C13 C14 C15 129.8(3)
C9 C14 C15 110.0(3)
O2 C15 C14 125.7(3)
O2 C15 C1 125.3(3)
C14 C15 C1 108.9(3)
O3 C16 O4 122.4(4)
O3 C16 C2 125.3(4)
O4 C16 C2 112.3(3)
C1 N1 C7 118.8(3)
C1 N1 C4 110.3(3)
C7 N1 C4 109.4(3)
C16 O4 C18 118.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.453(4)
C1 C15 1.553(5)
C1 C8 1.553(5)
C1 C2 1.579(5)
C2 C16 1.500(5)
C2 C3 1.527(5)
C2 C17 1.560(5)
C3 C4 1.514(6)
C4 N1 1.490(5)
C4 C5 1.536(7)
C5 C6 1.497(8)
C6 C7 1.511(7)
C7 N1 1.470(5)
C8 O1 1.219(4)
C8 C9 1.471(5)
C9 C10 1.381(5)
C9 C14 1.396(5)
C10 C11 1.389(6)
C11 C12 1.391(6)
C12 C13 1.377(6)
C13 C14 1.390(5)
C14 C15 1.475(5)
C15 O2 1.221(4)
C16 O3 1.215(5)
C16 O4 1.332(5)
C18 O4 1.444(5)
