#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:19:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180500 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/69/7216949.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_7216949
loop_
_publ_author_name
'Blockhuys, Frank'
'Hinchley, Sarah L.'
'Robertson, Heather E.'
'Blake, Alexander J.'
'McNab, Hamish'
'Despinoy, Xavier L. M.'
'Harris, Steven G.'
'Rankin, David W. H.'
_publ_section_title
;
 Pyrrolizin-3-one and its 1,2-dihydro derivative: structures of the free
 molecules determined by electron diffraction and ab initio calculations
 and in the crystal by X-ray diffractionElectronic supplementary
 information (ESI) available: further experimental data. See
 http://www.rsc.org/suppdata/p2/b1/b102475m/
;
_journal_issue                   11
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2195
_journal_paper_doi               10.1039/b102475m
_journal_year                    2001
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12
_chemical_name_systematic
; 
PYRROLIZIN-3-ONE
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 104.42(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.960(5)
_cell_length_b                   5.954(2)
_cell_length_c                   14.181(5)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      14.5
_cell_measurement_theta_min      12.5
_cell_volume                     1141.6(7)
_computing_cell_refinement       STADI-4
_computing_data_collection       STADI-4
_computing_data_reduction        X-RED
_computing_publication_material  'SHELXL-93; PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       omega/2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.021
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1756
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       'column within capillary tube'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.34
_refine_diff_density_rms         0.07
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²l³/sin(2q)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.037
_refine_ls_goodness_of_fit_obs   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_restrained_S_obs      1.042
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_obs          0.0531
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s²(Fo²)+( 0.108P)²+0.434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1676
_refine_ls_wR_factor_obs         0.1408
_reflns_number_observed          1342
_reflns_number_total             1674
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b102475m.txt
_cod_data_source_block           PYRRLZ
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.108P)^2^+0.434P] 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^)+( 0.108P)^2^+0.434P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7216949
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0300(6) 0.0240(6) 0.0199(5) -0.0002(4) 0.0063(4) 0.0052(5)
C2 0.0242(6) 0.0275(6) 0.0246(6) 0.0024(5) 0.0074(4) 0.0040(4)
C3 0.0221(5) 0.0228(6) 0.0202(5) 0.0016(4) 0.0031(4) -0.0005(4)
O3 0.0302(5) 0.0240(5) 0.0350(5) -0.0042(4) 0.0049(4) -0.0046(4)
N4 0.0205(5) 0.0200(5) 0.0203(5) -0.0022(4) 0.0030(3) 0.0002(3)
C5 0.0236(5) 0.0273(6) 0.0212(5) 0.0005(4) 0.0050(4) 0.0035(4)
C6 0.0230(6) 0.0351(7) 0.0239(6) 0.0010(5) 0.0043(4) -0.0012(5)
C7 0.0293(6) 0.0279(6) 0.0214(5) -0.0012(5) 0.0023(4) -0.0057(5)
C7a 0.0262(6) 0.0205(5) 0.0174(5) -0.0009(4) 0.0025(4) -0.0006(4)
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
C1 C 0.65887(10) 0.3908(2) 0.66303(9) 0.0246(3) Uani 1 d
H1 H 0.6481(14) 0.5301(35) 0.6922(14) 0.035(5) Uiso 1 d
C2 C 0.59289(9) 0.2298(2) 0.62556(9) 0.0252(3) Uani 1 d
H2 H 0.5212(14) 0.2279(32) 0.6213(13) 0.031(4) Uiso 1 d
C3 C 0.64402(9) 0.0439(2) 0.58755(9) 0.0221(3) Uani 1 d
O3 O 0.61273(7) -0.1325(2) 0.55040(7) 0.0303(3) Uani 1 d
N4 N 0.74323(7) 0.1149(2) 0.60665(7) 0.0207(3) Uani 1 d
C5 C 0.83140(9) 0.0446(2) 0.58838(9) 0.0241(3) Uani 1 d
H5 H 0.8337(14) -0.0962(30) 0.5549(14) 0.028(4) Uiso 1 d
C6 C 0.89948(9) 0.2085(2) 0.62295(9) 0.0276(3) Uani 1 d
H6 H 0.9680(14) 0.2073(35) 0.6157(13) 0.033(5) Uiso 1 d
C7 C 0.85159(10) 0.3857(2) 0.66271(9) 0.0269(3) Uani 1 d
H7 H 0.8786(13) 0.5266(34) 0.6922(13) 0.034(5) Uiso 1 d
C7a C 0.75541(9) 0.3229(2) 0.65112(8) 0.0219(3) Uani 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 C1 C7a 108.58(11)
C2 C1 H1 128.6(11)
C7a C1 H1 122.8(11)
C1 C2 C3 109.29(11)
C1 C2 H2 128.0(11)
C3 C2 H2 122.7(11)
O3 C3 N4 125.22(12)
O3 C3 C2 130.61(12)
N4 C3 C2 104.14(11)
C7a N4 C5 110.03(10)
C7a N4 C3 111.13(10)
C5 N4 C3 138.68(11)
C6 C5 N4 106.79(11)
C6 C5 H5 133.6(11)
N4 C5 H5 119.5(11)
C5 C6 C7 108.38(12)
C5 C6 H6 124.3(12)
C7 C6 H6 127.1(12)
C7a C7 C6 106.95(12)
C7a C7 H7 123.6(10)
C6 C7 H7 129.4(10)
C7 C7a N4 107.85(11)
C7 C7a C1 145.23(13)
N4 C7a C1 106.85(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.344(2)
C1 C7a 1.457(2)
C1 H1 0.96(2)
C2 C3 1.489(2)
C2 H2 0.99(2)
C3 O3 1.207(2)
C3 N4 1.408(2)
N4 C7a 1.381(2)
N4 C5 1.384(2)
C5 C6 1.365(2)
C5 H5 0.97(2)
C6 C7 1.437(2)
C6 H6 0.99(2)
C7 C7a 1.364(2)
C7 H7 0.97(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
C7a C1 C2 C3 0.62(14)
C1 C2 C3 O3 178.29(13)
C1 C2 C3 N4 -0.16(14)
O3 C3 N4 C7a -178.96(12)
C2 C3 N4 C7a -0.40(13)
O3 C3 N4 C5 6.5(2)
C2 C3 N4 C5 -174.90(13)
C7a N4 C5 C6 0.85(14)
C3 N4 C5 C6 175.39(14)
N4 C5 C6 C7 -0.61(15)
C5 C6 C7 C7a 0.2(2)
C6 C7 C7a N4 0.36(14)
C6 C7 C7a C1 -175.7(2)
C5 N4 C7a C7 -0.76(14)
C3 N4 C7a C7 -176.90(10)
C5 N4 C7a C1 176.90(9)
C3 N4 C7a C1 0.77(13)
C2 C1 C7a C7 175.2(2)
C2 C1 C7a N4 -0.86(14)
