#------------------------------------------------------------------------------
#$Date: 2018-10-05 14:19:55 +0200 (vie 05 de oct de 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/31/7213134.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_7213134
loop_
_publ_author_name
'McNab, Hamish'
'Parsons, Simon'
'Stevenson, Elizabeth'
_publ_section_title
;
 Pyrolytic cascades: a convenient entry to
 5H-pyrrolo[2,1-a]isoindol-5-ones and related heterocyclic systems
;
_journal_issue                   15
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2047
_journal_paper_doi               10.1039/a904885e
_journal_year                    1999
_chemical_formula_sum            'C11 H7 N O'
_chemical_formula_weight         169.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.3646(5)
_cell_length_b                   13.6245(14)
_cell_length_c                   22.377(2)
_cell_measurement_reflns_used    88
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      20
_cell_volume                     1635.5(3)
_computing_cell_refinement       'Stoe DIF4'
_computing_data_collection       'Stoe DIF4'
_computing_data_reduction        'Stoe REDU4'
_computing_molecular_graphics    SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      220(2)
_diffrn_measurement_device
; 
Stoe Stadi-4 diffractometer with 
Oxford Cryosystems variable temperature device. 
;
_diffrn_measurement_method       Omega-theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2653
_diffrn_reflns_theta_max         70.01
_diffrn_reflns_theta_min         3.95
_diffrn_standards_decay_%        -2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.719
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       Yellow
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.026
_refine_ls_goodness_of_fit_obs   1.063
_refine_ls_hydrogen_treatment    Riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_restrained_S_obs      1.063
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_obs          0.0357
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0541P)²+0.3176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0964
_refine_ls_wR_factor_obs         0.0906
_reflns_number_observed          1266
_reflns_number_total             1516
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904885esup1.cif
_cod_data_source_block           hmnes1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.3176P] 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^)+(0.0541P)^2^+0.3176P] where P=(Fo^2^+2Fc^2^)/3'.

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

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'Geometric' was changed to
'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7213134
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.0394(8) 0.0360(7) 0.0322(6) -0.0005(5) 0.0016(6) 0.0007(6)
C2 0.0362(7) 0.0369(7) 0.0420(7) 0.0025(6) -0.0006(6) -0.0032(6)
C3 0.0348(7) 0.0391(7) 0.0421(8) 0.0064(6) 0.0058(6) -0.0011(6)
N4 0.0366(6) 0.0382(6) 0.0305(6) 0.0009(4) 0.0061(5) 0.0009(5)
C5 0.0404(7) 0.0371(7) 0.0306(6) -0.0005(5) 0.0032(6) 0.0053(6)
O5 0.0568(7) 0.0560(7) 0.0332(5) -0.0051(4) 0.0127(5) -0.0006(6)
C5A 0.0364(7) 0.0344(7) 0.0319(6) 0.0006(5) 0.0023(6) 0.0040(6)
C6 0.0454(8) 0.0396(7) 0.0367(7) -0.0061(6) -0.0008(6) 0.0024(7)
C7 0.0416(8) 0.0392(8) 0.0494(8) -0.0042(6) -0.0009(7) -0.0052(7)
C8 0.0370(8) 0.0400(8) 0.0483(8) 0.0013(6) 0.0067(7) -0.0031(6)
C9 0.0395(7) 0.0362(7) 0.0346(6) -0.0014(5) 0.0060(6) 0.0004(6)
C9A 0.0326(7) 0.0300(6) 0.0318(6) 0.0001(5) 0.0011(5) 0.0037(5)
C9B 0.0328(7) 0.0336(7) 0.0298(6) 0.0023(5) 0.0041(5) 0.0033(6)
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
_atom_site_refinement_flags
C1 C 0.1975(3) 1.05204(10) 0.18984(6) 0.0358(3) Uani 1 d .
H1 H 0.1507(3) 1.06521(10) 0.22952(6) 0.043 Uiso 1 calc R
C2 C 0.3921(3) 1.09964(10) 0.15682(6) 0.0384(3) Uani 1 d .
H2 H 0.4958(3) 1.14986(10) 0.17134(6) 0.046 Uiso 1 calc R
C3 C 0.4018(3) 1.06023(10) 0.10114(6) 0.0387(4) Uani 1 d .
H3 H 0.5125(3) 1.07756(10) 0.07035(6) 0.046 Uiso 1 calc R
N4 N 0.2169(2) 0.98965(8) 0.09858(4) 0.0351(3) Uani 1 d .
C5 C 0.1245(3) 0.92261(10) 0.05644(5) 0.0360(3) Uani 1 d .
O5 O 0.1986(2) 0.91211(8) 0.00592(4) 0.0487(3) Uani 1 d .
C5A C -0.0782(3) 0.87063(10) 0.08864(6) 0.0342(3) Uani 1 d .
C6 C -0.2319(3) 0.79710(10) 0.06810(6) 0.0406(4) Uani 1 d .
H6 H -0.2174(3) 0.77315(10) 0.02886(6) 0.049 Uiso 1 calc R
C7 C -0.4087(3) 0.75941(11) 0.10703(7) 0.0434(4) Uani 1 d .
H7 H -0.5165(3) 0.70928(11) 0.09417(7) 0.052 Uiso 1 calc R
C8 C -0.4272(3) 0.79521(10) 0.16465(6) 0.0418(4) Uani 1 d .
H8 H -0.5484(3) 0.76870(10) 0.19036(6) 0.050 Uiso 1 calc R
C9 C -0.2716(3) 0.86946(10) 0.18578(6) 0.0368(3) Uani 1 d .
H9 H -0.2856(3) 0.89286(10) 0.22515(6) 0.044 Uiso 1 calc R
C9A C -0.0960(2) 0.90756(9) 0.14699(5) 0.0315(3) Uani 1 d .
C9B C 0.0935(3) 0.98425(9) 0.15288(5) 0.0320(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 0.0181 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
C9B C1 C2 107.02(12)
C3 C2 C1 108.77(12)
C2 C3 N4 106.60(12)
C3 N4 C9B 110.07(11)
C3 N4 C5 137.22(11)
C9B N4 C5 112.70(11)
O5 C5 N4 126.18(13)
O5 C5 C5A 129.76(13)
N4 C5 C5A 104.07(10)
C6 C5A C9A 122.10(13)
C6 C5A C5 128.60(12)
C9A C5A C5 109.30(11)
C5A C6 C7 118.00(13)
C8 C7 C6 120.31(14)
C7 C8 C9 121.95(13)
C9A C9 C8 117.88(12)
C9 C9A C5A 119.75(12)
C9 C9A C9B 133.23(12)
C5A C9A C9B 107.02(11)
C1 C9B N4 107.53(12)
C1 C9B C9A 145.56(12)
N4 C9B C9A 106.90(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9B 1.360(2)
C1 C2 1.434(2)
C2 C3 1.358(2)
C3 N4 1.383(2)
N4 C9B 1.386(2)
N4 C5 1.403(2)
C5 O5 1.2066(15)
C5 C5A 1.485(2)
C5A C6 1.376(2)
C5A C9A 1.402(2)
C6 C7 1.386(2)
C7 C8 1.382(2)
C8 C9 1.394(2)
C9 C9A 1.382(2)
C9A C9B 1.464(2)
