data_benzofuran
_audit_creation_date              2016-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C18 H16 O5'
_chemical_formula_sum             'C18 H16 O5'
_chemical_formula_weight          312.31
_chemical_melting_point           ?
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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                    11.0577(9)
_cell_length_b                    12.8224(10)
_cell_length_c                    11.7987(10)
_cell_angle_alpha                 90
_cell_angle_beta                  110.529(3)
_cell_angle_gamma                 90
_cell_volume                      1566.7(2)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     3688
_cell_measurement_temperature     303.4
_cell_measurement_theta_max       22.04
_cell_measurement_theta_min       2.43
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_T_max   0.7453
_exptl_absorpt_correction_T_min   0.6736
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0598 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.9038.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_modifier    .
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.324
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        plate
_exptl_crystal_F_000              656
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.05
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0740
_diffrn_reflns_av_unetI/netI      0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_number             21199
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full         26.000
_diffrn_reflns_theta_max          26.068
_diffrn_reflns_theta_min          2.433
_diffrn_ambient_temperature       303.4
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    ?
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1685
_reflns_number_total              3092
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection        ?
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.229
_refine_diff_density_min          -0.226
_refine_diff_density_rms          0.036
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      222
_refine_ls_number_reflns          3092
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1362
_refine_ls_R_factor_gt            0.0651
_refine_ls_restrained_S_all       1.032
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0723P)²+0.5864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1454
_refine_ls_wR_factor_ref          0.1766
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O14-C15A \\sim O14-C15
 with sigma of 0.005
3. Others
 Sof(C15)=Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C17(H17), C18(H18), C20(H20), C21(H21)
4.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C15A(H15A,H15B,H15C), C15(H15D,H15E,
 H15F)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.24708(18) 0.56193(16) 0.46486(17) 0.0631(6) Uani 1 1 d . . . . .
 O11 O 0.7466(2) 0.7060(2) 0.4490(2) 0.1068(9) Uani 1 1 d . . . . .
 O12 O 0.6727(2) 0.7255(2) 0.6000(2) 0.0885(8) Uani 1 1 d . . . . .
 O14 O 0.3897(3) 0.5175(3) 0.1293(3) 0.1129(10) Uani 1 1 d D . . . .
 O22 O 0.0186(2) 0.5889(2) 0.8853(2) 0.0874(8) Uani 1 1 d . . . . .
 C2 C 0.3045(3) 0.6117(2) 0.5765(2) 0.0546(7) Uani 1 1 d . . . . .
 C3 C 0.4189(3) 0.6527(2) 0.5838(3) 0.0580(7) Uani 1 1 d . . . . .
 H3 H 0.474625 0.690057 0.648761 0.070 Uiso 1 1 calc R . . . .
 C4 C 0.5356(3) 0.6440(2) 0.4231(3) 0.0593(7) Uani 1 1 d . . . . .
 C5 C 0.5151(3) 0.6063(2) 0.3076(3) 0.0702(9) Uani 1 1 d . . . . .
 H5 H 0.577806 0.617223 0.272949 0.084 Uiso 1 1 calc R . . . .
 C6 C 0.4041(3) 0.5532(2) 0.2431(3) 0.0706(9) Uani 1 1 d . . . . .
 C7 C 0.3099(3) 0.5345(2) 0.2889(3) 0.0681(8) Uani 1 1 d . . . . .
 H7 H 0.235565 0.497602 0.245910 0.082 Uiso 1 1 calc R . . . .
 C8 C 0.3305(3) 0.5736(2) 0.4035(3) 0.0596(7) Uani 1 1 d . . . . .
 C9 C 0.4395(3) 0.6287(2) 0.4738(2) 0.0531(7) Uani 1 1 d . . . . .
 C10 C 0.6615(3) 0.6948(3) 0.4893(3) 0.0733(9) Uani 1 1 d . . . . .
 C13 C 0.7961(4) 0.7716(4) 0.6720(4) 0.1266(17) Uani 1 1 d . . . . .
 H13A H 0.800749 0.841512 0.644708 0.190 Uiso 1 1 calc GR . . . .
 H13B H 0.865062 0.730859 0.663235 0.190 Uiso 1 1 calc GR . . . .
 H13C H 0.803708 0.772895 0.755619 0.190 Uiso 1 1 calc GR . . . .
 C16 C 0.2312(2) 0.6066(2) 0.6573(2) 0.0526(7) Uani 1 1 d . . . . .
 C17 C 0.2591(3) 0.6723(2) 0.7555(3) 0.0707(9) Uani 1 1 d . . . . .
 H17 H 0.325557 0.720556 0.769441 0.085 Uiso 1 1 calc R . . . .
 C18 C 0.1915(3) 0.6686(3) 0.8338(3) 0.0733(9) Uani 1 1 d . . . . .
 H18 H 0.213194 0.713278 0.899964 0.088 Uiso 1 1 calc R . . . .
 C19 C 0.0923(3) 0.5989(2) 0.8140(3) 0.0623(8) Uani 1 1 d . . . . .
 C20 C 0.0638(3) 0.5314(3) 0.7172(3) 0.0729(9) Uani 1 1 d . . . . .
 H20 H -0.002662 0.483213 0.703790 0.087 Uiso 1 1 calc R . . . .
 C21 C 0.1325(3) 0.5347(2) 0.6403(3) 0.0673(8) Uani 1 1 d . . . . .
 H21 H 0.112642 0.488149 0.575911 0.081 Uiso 1 1 calc R . . . .
 C23 C 0.0427(4) 0.6584(4) 0.9852(4) 0.1103(15) Uani 1 1 d . . . . .
 H23A H 0.031000 0.729045 0.956312 0.165 Uiso 1 1 calc GR . . . .
 H23B H 0.129636 0.649258 1.040120 0.165 Uiso 1 1 calc GR . . . .
 H23C H -0.016476 0.643800 1.026356 0.165 Uiso 1 1 calc GR . . . .
 C15A C 0.4643(8) 0.5215(7) 0.0686(7) 0.104(4) Uani 0.463(8) 1 d D . P A 1
 H15A H 0.482069 0.593012 0.056210 0.156 Uiso 0.463(8) 1 calc GR . P A 1
 H15B H 0.423502 0.488258 -0.008331 0.156 Uiso 0.463(8) 1 calc GR . P A 1
 H15C H 0.543627 0.486209 0.111977 0.156 Uiso 0.463(8) 1 calc GR . P A 1
 C15 C 0.3100(8) 0.4475(7) 0.0757(7) 0.121(4) Uani 0.537(8) 1 d D . P A 2
 H15D H 0.317854 0.389655 0.129463 0.181 Uiso 0.537(8) 1 calc GR . P A 2
 H15E H 0.327647 0.424570 0.005637 0.181 Uiso 0.537(8) 1 calc GR . P A 2
 H15F H 0.223968 0.475112 0.051291 0.181 Uiso 0.537(8) 1 calc GR . P A 2


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C2 1.400(3) . ?
 O1 C8 1.367(3) . ?
 C15Aa H15A 0.9600 . ?
 C15Aa H15B 0.9600 . ?
 C15Aa H15C 0.9600 . ?
 C15b H15D 0.9600 . ?
 C15b H15E 0.9600 . ?
 C15b H15F 0.9600 . ?
 O11 C10 1.202(3) . ?
 O12 C10 1.329(4) . ?
 O12 C13 1.456(4) . ?
 O14 C6 1.374(4) . ?
 O14 C15A 1.269(6) . ?
 O14 C15 1.261(6) . ?
 O22 C19 1.367(3) . ?
 O22 C23 1.427(4) . ?
 C2 C3 1.345(4) . ?
 C2 C16 1.453(4) . ?
 C3 H3 0.9300 . ?
 C3 C9 1.427(4) . ?
 C4 C5 1.388(4) . ?
 C4 C9 1.404(4) . ?
 C4 C10 1.487(4) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.377(4) . ?
 C6 C7 1.353(4) . ?
 C7 H7 0.9300 . ?
 C7 C8 1.383(4) . ?
 C8 C9 1.392(4) . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?
 C16 C17 1.377(4) . ?
 C16 C21 1.388(4) . ?
 C17 H17 0.9300 . ?
 C17 C18 1.378(4) . ?
 C18 H18 0.9300 . ?
 C18 C19 1.369(4) . ?
 C19 C20 1.379(4) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.373(4) . ?
 C21 H21 0.9300 . ?
 C23 H23A 0.9600 . ?
 C23 H23B 0.9600 . ?
 C23 H23C 0.9600 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C8 O1 C2 106.3(2) . . ?
 H15Aa C15Aa H15B 109.5 . . ?
 H15Ba C15Aa H15C 109.5 . . ?
 C10 O12 C13 116.1(3) . . ?
 C19 O22 C23 118.1(3) . . ?
 O1 C2 C16 115.1(2) . . ?
 C3 C2 O1 110.2(2) . . ?
 C3 C2 C16 134.8(3) . . ?
 C2 C3 H3 126.1 . . ?
 C2 C3 C9 107.7(3) . . ?
 C9 C3 H3 126.1 . . ?
 H15Aa C15Aa H15C 109.5 . . ?
 H15Db C15b H15E 109.5 . . ?
 H15Eb C15b H15F 109.5 . . ?
 H15Db C15b H15F 109.5 . . ?
 C15b O14 C6 123.3(5) . . ?
 C15Aa O14 C6 131.5(5) . . ?
 C5 C4 C9 118.9(3) . . ?
 C5 C4 C10 118.0(3) . . ?
 C9 C4 C10 123.1(3) . . ?
 C4 C5 H5 119.3 . . ?
 C6 C5 C4 121.4(3) . . ?
 C6 C5 H5 119.3 . . ?
 O14 C6 C5 118.7(3) . . ?
 C7 C6 O14 119.3(3) . . ?
 C7 C6 C5 122.0(3) . . ?
 C6 C7 H7 122.0 . . ?
 C6 C7 C8 116.1(3) . . ?
 C8 C7 H7 122.0 . . ?
 O1 C8 C7 124.6(3) . . ?
 O1 C8 C9 110.1(2) . . ?
 C7 C8 C9 125.3(3) . . ?
 C4 C9 C3 138.0(3) . . ?
 C8 C9 C3 105.7(2) . . ?
 C8 C9 C4 116.3(3) . . ?
 O11 C10 O12 122.5(3) . . ?
 O11 C10 C4 124.3(3) . . ?
 O12 C10 C4 113.2(3) . . ?
 O12 C13 H13A 109.5 . . ?
 O12 C13 H13B 109.5 . . ?
 O12 C13 H13C 109.5 . . ?
 O14 C15Aa H15A 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?
 C17 C16 C2 120.8(2) . . ?
 C17 C16 C21 117.4(3) . . ?
 C21 C16 C2 121.7(3) . . ?
 C16 C17 H17 119.1 . . ?
 C16 C17 C18 121.9(3) . . ?
 O14 C15Aa H15B 109.5 . . ?
 O14 C15Aa H15C 109.5 . . ?
 O14 C15b H15D 109.5 . . ?
 O14 C15b H15E 109.5 . . ?
 O14 C15b H15F 109.5 . . ?
 C18 C17 H17 119.1 . . ?
 C17 C18 H18 120.0 . . ?
 C19 C18 C17 119.9(3) . . ?
 C19 C18 H18 120.0 . . ?
 O22 C19 C18 124.8(3) . . ?
 O22 C19 C20 116.0(3) . . ?
 C18 C19 C20 119.2(3) . . ?
 C19 C20 H20 119.7 . . ?
 C21 C20 C19 120.6(3) . . ?
 C21 C20 H20 119.7 . . ?
 C16 C21 H21 119.5 . . ?
 C20 C21 C16 121.0(3) . . ?
 C20 C21 H21 119.5 . . ?
 O22 C23 H23A 109.5 . . ?
 O22 C23 H23B 109.5 . . ?
 O22 C23 H23C 109.5 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?

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
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 C15b O14 C6 C5 161.8(6) . . . . ?
 C15Aa O14 C6 C5 2.2(8) . . . . ?
 C15b O14 C6 C7 -17.7(7) . . . . ?
 C15Aa O14 C6 C7 -177.3(6) . . . . ?
 O1 C2 C3 C9 -0.6(3) . . . . ?
 O1 C2 C16 C17 -164.0(3) . . . . ?
 O1 C2 C16 C21 17.2(4) . . . . ?
 O1 C8 C9 C3 -0.8(3) . . . . ?
 O1 C8 C9 C4 178.3(2) . . . . ?
 O14 C6 C7 C8 -179.4(3) . . . . ?
 O22 C19 C20 C21 -179.7(3) . . . . ?
 C2 O1 C8 C7 179.5(3) . . . . ?
 C2 O1 C8 C9 0.5(3) . . . . ?
 C2 C3 C9 C4 -177.9(3) . . . . ?
 C2 C3 C9 C8 0.9(3) . . . . ?
 C2 C16 C17 C18 -179.6(3) . . . . ?
 C2 C16 C21 C20 -179.6(3) . . . . ?
 C3 C2 C16 C17 17.3(5) . . . . ?
 C3 C2 C16 C21 -161.5(3) . . . . ?
 C4 C5 C6 O14 -179.8(3) . . . . ?
 C4 C5 C6 C7 -0.3(5) . . . . ?
 C5 C4 C9 C3 -179.8(3) . . . . ?
 C5 C4 C9 C8 1.5(4) . . . . ?
 C5 C4 C10 O11 0.5(5) . . . . ?
 C5 C4 C10 O12 -178.2(3) . . . . ?
 C5 C6 C7 C8 1.1(5) . . . . ?
 C6 C7 C8 O1 -179.4(3) . . . . ?
 C6 C7 C8 C9 -0.6(5) . . . . ?
 C7 C8 C9 C3 -179.8(3) . . . . ?
 C7 C8 C9 C4 -0.7(4) . . . . ?
 C8 O1 C2 C3 0.1(3) . . . . ?
 C8 O1 C2 C16 -179.0(2) . . . . ?
 C9 C4 C5 C6 -1.0(4) . . . . ?
 C9 C4 C10 O11 177.8(3) . . . . ?
 C9 C4 C10 O12 -1.0(4) . . . . ?
 C10 C4 C5 C6 176.3(3) . . . . ?
 C10 C4 C9 C3 3.0(5) . . . . ?
 C10 C4 C9 C8 -175.7(3) . . . . ?
 C13 O12 C10 O11 -1.5(5) . . . . ?
 C13 O12 C10 C4 177.3(3) . . . . ?
 C16 C2 C3 C9 178.2(3) . . . . ?
 C16 C17 C18 C19 -0.8(5) . . . . ?
 C17 C16 C21 C20 1.5(4) . . . . ?
 C17 C18 C19 O22 -179.7(3) . . . . ?
 C17 C18 C19 C20 1.7(5) . . . . ?
 C18 C19 C20 C21 -0.9(5) . . . . ?
 C19 C20 C21 C16 -0.7(5) . . . . ?
 C21 C16 C17 C18 -0.8(5) . . . . ?
 C23 O22 C19 C18 2.6(5) . . . . ?
 C23 O22 C19 C20 -178.7(3) . . . . ?

_shelx_SHELXL_version_number      '2016/4'
_olex2_submission_special_instructions 'No special instructions were received'
