#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/86/2218651.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2218651
loop_
_publ_author_name
'Feng, Mei-Li'
'Li, Yu-Feng'
'Liu, Shan'
'Yang, Hai-Yu'
'Zhu, Hong-Jun'
_publ_section_title
;
 2-Methyl-7-nitro-2,3-dihydro-1-benzofuran
;
_journal_coeditor_code           CI2613
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1281
_journal_paper_doi               10.1107/S1600536808017728
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C9 H9 N O3'
_chemical_formula_moiety         'C9 H9 N O3'
_chemical_formula_sum            'C9 H9 N O3'
_chemical_formula_weight         179.17
_chemical_name_systematic
;
2-Methyl-7-nitro-2,3-dihydro-1-benzofuran
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4250(17)
_cell_length_b                   7.2260(14)
_cell_length_c                   28.295(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1722.6(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2977
_diffrn_reflns_theta_full        25.21
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.06P)²+1.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1823
_reflns_number_gt                829
_reflns_number_total             1551
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2613.cif
_cod_data_source_block           I
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2218651
_cod_database_fobs_code          2218651
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N 0.5181(3) 0.0623(5) 0.39917(10) 0.0581(8) Uani d . 1
O O1 0.2624(3) 0.0149(4) 0.32787(7) 0.0601(8) Uani d . 1
C C1 0.1077(6) 0.0403(8) 0.25775(16) 0.0970(16) Uani d . 1
H H1A 0.1909 -0.0204 0.2405 0.146 Uiso calc R 1
H H1B 0.1258 0.1715 0.2576 0.146 Uiso calc R 1
H H1C 0.0074 0.0140 0.2431 0.146 Uiso calc R 1
O O2 0.5612(3) 0.0409(5) 0.35839(9) 0.0867(10) Uani d . 1
C C2 0.1064(4) -0.0249(8) 0.30507(14) 0.0812(14) Uani d . 1
H H2A 0.0947 -0.1598 0.3038 0.097 Uiso calc R 1
O O3 0.6098(3) 0.0689(6) 0.43222(10) 0.0992(12) Uani d . 1
C C3 -0.0172(4) 0.0473(6) 0.33963(14) 0.0706(11) Uani d . 1
H H3A -0.0614 0.1638 0.3289 0.085 Uiso calc R 1
H H3B -0.1025 -0.0413 0.3438 0.085 Uiso calc R 1
C C4 0.0753(4) 0.0725(5) 0.38480(12) 0.0532(9) Uani d . 1
C C5 0.0285(4) 0.1112(5) 0.42971(13) 0.0634(10) Uani d . 1
H H5A -0.0788 0.1240 0.4368 0.076 Uiso calc R 1
C C6 0.1416(5) 0.1314(6) 0.46479(13) 0.0624(10) Uani d . 1
H H6A 0.1093 0.1557 0.4956 0.075 Uiso calc R 1
C C7 0.3000(4) 0.1164(5) 0.45498(12) 0.0560(9) Uani d . 1
H H7A 0.3747 0.1319 0.4789 0.067 Uiso calc R 1
C C8 0.3491(4) 0.0774(5) 0.40863(11) 0.0460(8) Uani d . 1
C C9 0.2360(4) 0.0537(4) 0.37377(11) 0.0459(8) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N 0.0376(15) 0.085(2) 0.0513(17) -0.0068(16) -0.0090(16) 0.0044(16)
O1 0.0358(11) 0.104(2) 0.0411(12) 0.0006(13) -0.0058(12) -0.0061(12)
C1 0.066(3) 0.151(5) 0.074(3) -0.004(3) -0.022(3) 0.017(3)
O2 0.0389(13) 0.168(3) 0.0530(16) 0.0016(17) 0.0045(13) -0.0016(17)
C2 0.047(2) 0.134(4) 0.063(2) -0.004(2) -0.014(2) -0.002(3)
O3 0.0446(15) 0.176(3) 0.0773(19) -0.0046(19) -0.0248(16) -0.009(2)
C3 0.0399(19) 0.098(3) 0.074(3) -0.003(2) -0.009(2) -0.002(2)
C4 0.0313(16) 0.070(2) 0.058(2) 0.0012(16) 0.0062(16) 0.0053(18)
C5 0.044(2) 0.069(3) 0.077(3) 0.0068(18) 0.009(2) 0.004(2)
C6 0.069(2) 0.073(2) 0.0458(19) 0.006(2) 0.011(2) -0.0021(18)
C7 0.060(2) 0.061(2) 0.047(2) -0.0053(19) -0.0032(18) 0.0004(17)
C8 0.0352(17) 0.060(2) 0.0426(18) -0.0023(15) -0.0007(15) 0.0044(16)
C9 0.0375(16) 0.0554(19) 0.0447(17) -0.0043(15) -0.0028(16) 0.0030(16)
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
O3 N O2 123.0(3)
O3 N C8 118.6(3)
O2 N C8 118.4(3)
C9 O1 C2 108.2(3)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C1 C2 O1 109.7(4)
C1 C2 C3 119.9(4)
O1 C2 C3 105.0(3)
C1 C2 H2A 107.2
O1 C2 H2A 107.2
C3 C2 H2A 107.2
C4 C3 C2 103.5(3)
C4 C3 H3A 111.1
C2 C3 H3A 111.1
C4 C3 H3B 111.1
C2 C3 H3B 111.1
H3A C3 H3B 109.0
C5 C4 C9 120.7(3)
C5 C4 C3 131.8(3)
C9 C4 C3 107.5(3)
C4 C5 C6 119.5(3)
C4 C5 H5A 120.3
C6 C5 H5A 120.3
C7 C6 C5 121.2(3)
C7 C6 H6A 119.4
C5 C6 H6A 119.4
C6 C7 C8 119.6(3)
C6 C7 H7A 120.2
C8 C7 H7A 120.2
C9 C8 C7 119.2(3)
C9 C8 N 122.3(3)
C7 C8 N 118.4(3)
O1 C9 C8 126.9(3)
O1 C9 C4 113.3(3)
C8 C9 C4 119.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N O3 1.214(4)
N O2 1.219(3)
N C8 1.453(4)
O1 C9 1.347(4)
O1 C2 1.492(4)
C1 C2 1.420(6)
C1 H1A 0.96
C1 H1B 0.96
C1 H1C 0.96
C2 C3 1.520(6)
C2 H2A 0.98
C3 C4 1.508(5)
C3 H3A 0.97
C3 H3B 0.97
C4 C5 1.360(5)
C4 C9 1.396(4)
C5 C6 1.384(5)
C5 H5A 0.93
C6 C7 1.367(5)
C6 H6A 0.93
C7 C8 1.404(4)
C7 H7A 0.93
C8 C9 1.382(4)
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
C9 O1 C2 C1 145.4(4)
C9 O1 C2 C3 15.4(4)
C1 C2 C3 C4 -139.3(4)
O1 C2 C3 C4 -15.5(5)
C2 C3 C4 C5 -170.7(4)
C2 C3 C4 C9 10.9(5)
C9 C4 C5 C6 -0.2(6)
C3 C4 C5 C6 -178.4(4)
C4 C5 C6 C7 1.2(6)
C5 C6 C7 C8 -0.8(6)
C6 C7 C8 C9 -0.4(5)
C6 C7 C8 N 180.0(3)
O3 N C8 C9 -173.7(3)
O2 N C8 C9 5.3(5)
O3 N C8 C7 5.9(5)
O2 N C8 C7 -175.1(3)
C2 O1 C9 C8 172.0(4)
C2 O1 C9 C4 -8.9(4)
C7 C8 C9 O1 -179.7(3)
N C8 C9 O1 0.0(6)
C7 C8 C9 C4 1.3(5)
N C8 C9 C4 -179.1(3)
C5 C4 C9 O1 179.8(3)
C3 C4 C9 O1 -1.6(4)
C5 C4 C9 C8 -1.0(6)
C3 C4 C9 C8 177.6(3)
