# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c0310m
_database_code_depnum_ccdc_archive 'CCDC 1508863'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(S)-1-(6-Methoxybenzofuran-2-yl)-2-nitroethanol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O10'
_chemical_formula_weight         474.42

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.993(4)
_cell_length_b                   12.540(5)
_cell_length_c                   10.604(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.751(8)
_cell_angle_gamma                90.00
_cell_volume                     1036.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    446(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      446(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6640
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         29.08
_reflns_number_total             4338
_reflns_number_gt                3272
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.3(14)
_refine_ls_number_reflns         4338
_refine_ls_number_parameters     315
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3277(3) 0.7181(2) 0.5477(3) 0.0369(6) Uani 1 1 d D . .
H1 H 0.294(5) 0.7776(17) 0.513(3) 0.044 Uiso 1 1 d D . .
O2 O -0.0159(6) 0.8482(3) 0.5092(3) 0.0846(14) Uani 1 1 d . . .
O3 O -0.0562(4) 0.7435(3) 0.3520(3) 0.0603(9) Uani 1 1 d . . .
O4 O 0.4118(3) 0.63350(17) 0.8164(2) 0.0314(6) Uani 1 1 d . . .
O5 O 0.7038(4) 0.4254(2) 1.1746(2) 0.0413(7) Uani 1 1 d . . .
O6 O 0.2682(3) 0.5674(2) 0.3525(2) 0.0348(6) Uani 1 1 d D . .
H6 H 0.235(5) 0.606(3) 0.287(3) 0.052 Uiso 1 1 d D . .
O7 O 0.6692(6) 0.5248(3) 0.6192(4) 0.0840(13) Uani 1 1 d . . .
O8 O 0.6368(4) 0.6137(3) 0.4473(3) 0.0578(9) Uani 1 1 d . . .
O9 O 0.1704(3) 0.43049(18) 0.1432(2) 0.0339(6) Uani 1 1 d . . .
O10 O -0.2267(3) 0.2221(2) -0.1606(2) 0.0390(7) Uani 1 1 d . . .
N1 N -0.0163(5) 0.7619(3) 0.4639(4) 0.0457(9) Uani 1 1 d . . .
N2 N 0.6101(4) 0.5377(3) 0.5074(4) 0.0439(9) Uani 1 1 d . . .
C1 C 0.2169(5) 0.6951(3) 0.6309(3) 0.0330(8) Uani 1 1 d . . .
H1A H 0.2101 0.7587 0.6833 0.040 Uiso 1 1 calc R . .
C2 C 0.0404(5) 0.6714(3) 0.5532(4) 0.0408(10) Uani 1 1 d . . .
H2B H 0.0417 0.6062 0.5043 0.049 Uiso 1 1 calc R . .
H2A H -0.0381 0.6621 0.6102 0.049 Uiso 1 1 calc R . .
C3 C 0.8190(5) 0.5075(4) 1.2227(4) 0.0480(11) Uani 1 1 d . . .
H3C H 0.8822 0.5267 1.1589 0.072 Uiso 1 1 calc R . .
H3B H 0.8971 0.4837 1.2998 0.072 Uiso 1 1 calc R . .
H3A H 0.7567 0.5685 1.2424 0.072 Uiso 1 1 calc R . .
C4 C 0.2787(5) 0.6070(3) 0.7181(3) 0.0309(8) Uani 1 1 d . . .
C5 C 0.2334(5) 0.5056(3) 0.7260(3) 0.0322(8) Uani 1 1 d . . .
H5 H 0.1469 0.4693 0.6691 0.039 Uiso 1 1 calc R . .
C6 C 0.3442(5) 0.4641(3) 0.8392(3) 0.0277(8) Uani 1 1 d . . .
C7 C 0.3656(5) 0.3678(3) 0.9031(4) 0.0348(9) Uani 1 1 d . . .
H7 H 0.2972 0.3096 0.8710 0.042 Uiso 1 1 calc R . .
C8 C 0.4879(6) 0.3591(3) 1.0137(4) 0.0375(9) Uani 1 1 d . . .
H8 H 0.5030 0.2943 1.0574 0.045 Uiso 1 1 calc R . .
C9 C 0.5895(5) 0.4438(3) 1.0623(3) 0.0314(8) Uani 1 1 d . . .
C10 C 0.5738(5) 0.5397(3) 1.0009(3) 0.0324(9) Uani 1 1 d . . .
H10 H 0.6434 0.5976 1.0324 0.039 Uiso 1 1 calc R . .
C11 C 0.4493(5) 0.5454(3) 0.8900(3) 0.0288(8) Uani 1 1 d . . .
C12 C 0.3797(5) 0.4890(3) 0.3222(4) 0.0320(8) Uani 1 1 d . . .
H12 H 0.4515 0.5210 0.2684 0.038 Uiso 1 1 calc R . .
C13 C 0.4896(5) 0.4527(3) 0.4450(4) 0.0417(10) Uani 1 1 d . . .
H13B H 0.5549 0.3910 0.4288 0.050 Uiso 1 1 calc R . .
H13A H 0.4180 0.4313 0.5034 0.050 Uiso 1 1 calc R . .
C14 C -0.2884(6) 0.3122(3) -0.2373(4) 0.0425(10) Uani 1 1 d . . .
H14C H -0.3817 0.2912 -0.3064 0.064 Uiso 1 1 calc R . .
H14B H -0.1977 0.3415 -0.2727 0.064 Uiso 1 1 calc R . .
H14A H -0.3275 0.3649 -0.1848 0.064 Uiso 1 1 calc R . .
C15 C 0.2824(5) 0.3998(3) 0.2518(4) 0.0321(8) Uani 1 1 d . . .
C16 C 0.2774(5) 0.2962(3) 0.2713(3) 0.0308(8) Uani 1 1 d . . .
H16 H 0.3439 0.2577 0.3392 0.037 Uiso 1 1 calc R . .
C17 C 0.1491(5) 0.2552(3) 0.1671(3) 0.0306(8) Uani 1 1 d . . .
C18 C 0.0790(5) 0.1571(3) 0.1288(4) 0.0346(9) Uani 1 1 d . . .
H18 H 0.1186 0.0960 0.1757 0.041 Uiso 1 1 calc R . .
C19 C -0.0492(5) 0.1511(3) 0.0211(3) 0.0340(9) Uani 1 1 d . . .
H19 H -0.1015 0.0857 -0.0028 0.041 Uiso 1 1 calc R . .
C20 C -0.1035(5) 0.2396(3) -0.0538(3) 0.0295(8) Uani 1 1 d . . .
C21 C -0.0351(5) 0.3374(3) -0.0187(4) 0.0334(8) Uani 1 1 d . . .
H21 H -0.0711 0.3983 -0.0673 0.040 Uiso 1 1 calc R . .
C22 C 0.0892(5) 0.3407(3) 0.0921(3) 0.0281(8) Uani 1 1 d . . .


_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 C1 1.411(5) . ?
O1 H1 0.846(10) . ?
O2 N1 1.184(5) . ?
O3 N1 1.181(4) . ?
O4 C11 1.347(4) . ?
O4 C4 1.356(4) . ?
O5 C9 1.351(4) . ?
O5 C3 1.401(5) . ?
O6 C12 1.411(4) . ?
O6 H6 0.845(10) . ?
O7 N2 1.187(4) . ?
O8 N2 1.192(5) . ?
O9 C15 1.349(4) . ?
O9 C22 1.352(4) . ?
O10 C20 1.344(4) . ?
O10 C14 1.416(5) . ?
N1 C2 1.483(5) . ?
N2 C13 1.489(5) . ?
C1 C4 1.455(5) . ?
C1 C2 1.498(5) . ?
C1 H1A 0.9800 . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
C3 H3C 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3A 0.9600 . ?
C4 C5 1.330(5) . ?
C5 C6 1.424(5) . ?
C5 H5 0.9300 . ?
C6 C11 1.355(5) . ?
C6 C7 1.377(5) . ?
C7 C8 1.355(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.361(5) . ?
C10 C11 1.365(5) . ?
C10 H10 0.9300 . ?
C12 C15 1.468(5) . ?
C12 C13 1.473(5) . ?
C12 H12 0.9800 . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C14 H14C 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14A 0.9600 . ?
C15 C16 1.317(5) . ?
C16 C17 1.427(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.358(5) . ?
C17 C18 1.375(5) . ?
C18 C19 1.357(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.361(5) . ?
C21 C22 1.362(5) . ?
C21 H21 0.9300 . ?

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
C1 O1 H1 105(3) . . ?
C11 O4 C4 106.3(3) . . ?
C9 O5 C3 117.3(3) . . ?
C12 O6 H6 108(3) . . ?
C15 O9 C22 105.9(3) . . ?
C20 O10 C14 116.8(3) . . ?
O3 N1 O2 124.2(4) . . ?
O3 N1 C2 118.0(4) . . ?
O2 N1 C2 117.8(4) . . ?
O7 N2 O8 124.4(4) . . ?
O7 N2 C13 115.0(4) . . ?
O8 N2 C13 120.6(3) . . ?
O1 C1 C4 112.4(3) . . ?
O1 C1 C2 110.0(3) . . ?
C4 C1 C2 110.2(3) . . ?
O1 C1 H1A 108.1 . . ?
C4 C1 H1A 108.1 . . ?
C2 C1 H1A 108.1 . . ?
N1 C2 C1 108.5(3) . . ?
N1 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
N1 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
H2B C2 H2A 108.4 . . ?
O5 C3 H3C 109.5 . . ?
O5 C3 H3B 109.5 . . ?
H3C C3 H3B 109.5 . . ?
O5 C3 H3A 109.5 . . ?
H3C C3 H3A 109.5 . . ?
H3B C3 H3A 109.5 . . ?
C5 C4 O4 111.4(3) . . ?
C5 C4 C1 135.0(3) . . ?
O4 C4 C1 113.7(3) . . ?
C4 C5 C6 106.0(3) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
C11 C6 C7 117.8(3) . . ?
C11 C6 C5 106.0(3) . . ?
C7 C6 C5 136.3(3) . . ?
C8 C7 C6 118.9(4) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
O5 C9 C10 123.1(3) . . ?
O5 C9 C8 115.4(3) . . ?
C10 C9 C8 121.5(3) . . ?
C9 C10 C11 115.6(3) . . ?
C9 C10 H10 122.2 . . ?
C11 C10 H10 122.2 . . ?
O4 C11 C6 110.4(3) . . ?
O4 C11 C10 124.7(3) . . ?
C6 C11 C10 125.0(3) . . ?
O6 C12 C15 110.9(3) . . ?
O6 C12 C13 107.3(3) . . ?
C15 C12 C13 111.1(3) . . ?
O6 C12 H12 109.2 . . ?
C15 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
C12 C13 N2 111.9(3) . . ?
C12 C13 H13B 109.2 . . ?
N2 C13 H13B 109.2 . . ?
C12 C13 H13A 109.2 . . ?
N2 C13 H13A 109.2 . . ?
H13B C13 H13A 107.9 . . ?
O10 C14 H14C 109.5 . . ?
O10 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
O10 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
C16 C15 O9 112.2(3) . . ?
C16 C15 C12 134.6(4) . . ?
O9 C15 C12 113.2(3) . . ?
C15 C16 C17 106.0(3) . . ?
C15 C16 H16 127.0 . . ?
C17 C16 H16 127.0 . . ?
C22 C17 C18 117.7(3) . . ?
C22 C17 C16 105.6(3) . . ?
C18 C17 C16 136.7(3) . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.6(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
O10 C20 C21 123.6(3) . . ?
O10 C20 C19 115.6(3) . . ?
C21 C20 C19 120.8(3) . . ?
C20 C21 C22 115.8(3) . . ?
C20 C21 H21 122.1 . . ?
C22 C21 H21 122.1 . . ?
O9 C22 C17 110.3(3) . . ?
O9 C22 C21 124.4(3) . . ?
C17 C22 C21 125.3(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 N1 C2 C1 122.9(4) . . . . ?
O2 N1 C2 C1 -55.8(5) . . . . ?
O1 C1 C2 N1 -54.4(4) . . . . ?
C4 C1 C2 N1 -178.8(3) . . . . ?
C11 O4 C4 C5 -1.0(4) . . . . ?
C11 O4 C4 C1 177.8(3) . . . . ?
O1 C1 C4 C5 -106.3(5) . . . . ?
C2 C1 C4 C5 16.7(6) . . . . ?
O1 C1 C4 O4 75.2(4) . . . . ?
C2 C1 C4 O4 -161.8(3) . . . . ?
O4 C4 C5 C6 0.9(4) . . . . ?
C1 C4 C5 C6 -177.6(4) . . . . ?
C4 C5 C6 C11 -0.4(4) . . . . ?
C4 C5 C6 C7 179.3(4) . . . . ?
C11 C6 C7 C8 0.9(5) . . . . ?
C5 C6 C7 C8 -178.8(4) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C3 O5 C9 C10 -5.1(5) . . . . ?
C3 O5 C9 C8 175.3(4) . . . . ?
C7 C8 C9 O5 178.6(3) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
O5 C9 C10 C11 -178.5(3) . . . . ?
C8 C9 C10 C11 1.0(6) . . . . ?
C4 O4 C11 C6 0.7(4) . . . . ?
C4 O4 C11 C10 -178.4(4) . . . . ?
C7 C6 C11 O4 -180.0(3) . . . . ?
C5 C6 C11 O4 -0.2(4) . . . . ?
C7 C6 C11 C10 -0.9(6) . . . . ?
C5 C6 C11 C10 178.9(4) . . . . ?
C9 C10 C11 O4 178.9(3) . . . . ?
C9 C10 C11 C6 -0.1(6) . . . . ?
O6 C12 C13 N2 -68.0(4) . . . . ?
C15 C12 C13 N2 170.7(3) . . . . ?
O7 N2 C13 C12 161.2(4) . . . . ?
O8 N2 C13 C12 -16.1(5) . . . . ?
C22 O9 C15 C16 0.6(4) . . . . ?
C22 O9 C15 C12 -178.6(3) . . . . ?
O6 C12 C15 C16 -122.6(5) . . . . ?
C13 C12 C15 C16 -3.4(6) . . . . ?
O6 C12 C15 O9 56.2(4) . . . . ?
C13 C12 C15 O9 175.4(3) . . . . ?
O9 C15 C16 C17 -0.8(5) . . . . ?
C12 C15 C16 C17 178.1(4) . . . . ?
C15 C16 C17 C22 0.7(4) . . . . ?
C15 C16 C17 C18 -179.4(4) . . . . ?
C22 C17 C18 C19 -2.0(5) . . . . ?
C16 C17 C18 C19 178.2(4) . . . . ?
C17 C18 C19 C20 3.5(6) . . . . ?
C14 O10 C20 C21 -1.3(5) . . . . ?
C14 O10 C20 C19 178.3(3) . . . . ?
C18 C19 C20 O10 177.5(3) . . . . ?
C18 C19 C20 C21 -2.9(6) . . . . ?
O10 C20 C21 C22 -179.7(3) . . . . ?
C19 C20 C21 C22 0.8(6) . . . . ?
C15 O9 C22 C17 -0.1(4) . . . . ?
C15 O9 C22 C21 179.8(3) . . . . ?
C18 C17 C22 O9 179.7(3) . . . . ?
C16 C17 C22 O9 -0.4(4) . . . . ?
C18 C17 C22 C21 -0.1(6) . . . . ?
C16 C17 C22 C21 179.8(4) . . . . ?
C20 C21 C22 O9 -179.1(4) . . . . ?
C20 C21 C22 C17 0.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc-Hexane'
_chemical_properties_physical    ', Heat-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sad
_database_code_depnum_ccdc_archive 'CCDC 1508862'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(S)-1-(5-Chlorobenzofuran-2-yl)-2-nitroethanol
_chemical_name_common            'Chloride substitute'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Cl N O4'
_chemical_formula_weight         241.62

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.5571(2)
_cell_length_b                   5.6305(2)
_cell_length_c                   32.3624(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1012.60(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    35
_cell_measurement_theta_min      34
_cell_measurement_theta_max      36

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    3.371
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5521
_exptl_absorpt_correction_T_max  0.7742
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Gemini Oxford Diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         5.47
_diffrn_reflns_theta_max         62.12
_reflns_number_total             1590
_reflns_number_gt                1505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0378P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(12)
_refine_ls_number_reflns         1590
_refine_ls_number_parameters     148
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.40402(8) 1.17237(9) 0.965057(12) 0.03712(14) Uani 1 1 d . . .
O1 O 0.5933(2) 0.72204(19) 0.88253(3) 0.0266(3) Uani 1 1 d . . .
O2 O 0.3006(2) 1.0329(2) 0.79958(4) 0.0383(3) Uani 1 1 d D . .
O3 O 0.1533(2) 0.4953(3) 0.74362(4) 0.0413(3) Uani 1 1 d . . .
O4 O -0.0316(2) 0.5237(2) 0.80189(4) 0.0388(3) Uani 1 1 d . . .
C1 C 0.5530(3) 0.8878(3) 0.85215(5) 0.0246(4) Uani 1 1 d . . .
C2 C 0.7095(3) 1.0691(3) 0.85342(5) 0.0248(4) Uani 1 1 d . . .
H2A H 0.7157 1.1988 0.8357 0.030 Uiso 1 1 calc R . .
C3 C 0.8665(3) 1.0216(3) 0.88806(5) 0.0225(3) Uani 1 1 d . . .
C4 C 1.0612(3) 1.1385(3) 0.90632(5) 0.0256(3) Uani 1 1 d . . .
H4A H 1.1189 1.2817 0.8960 0.031 Uiso 1 1 calc R . .
C5 C 1.1642(3) 1.0315(3) 0.94047(5) 0.0268(4) Uani 1 1 d . . .
C6 C 1.0848(3) 0.8136(3) 0.95623(5) 0.0309(4) Uani 1 1 d . . .
H6A H 1.1621 0.7464 0.9789 0.037 Uiso 1 1 calc R . .
C7 C 0.8917(3) 0.6979(3) 0.93825(5) 0.0297(4) Uani 1 1 d . . .
H7A H 0.8345 0.5541 0.9484 0.036 Uiso 1 1 calc R . .
C8 C 0.7886(3) 0.8065(3) 0.90456(5) 0.0250(3) Uani 1 1 d . . .
C9 C 0.3391(3) 0.8348(3) 0.82560(5) 0.0253(3) Uani 1 1 d D . .
H9A H 0.1978 0.8137 0.8434 0.030 Uiso 1 1 calc R . .
N1 N 0.1497(2) 0.5371(2) 0.78065(4) 0.0264(3) Uani 1 1 d . . .
C10 C 0.3795(3) 0.6088(3) 0.80105(5) 0.0265(3) Uani 1 1 d . . .
H10A H 0.5027 0.6351 0.7803 0.032 Uiso 1 1 calc R . .
H10B H 0.4339 0.4831 0.8193 0.032 Uiso 1 1 calc R . .
H1 H 0.163(2) 1.015(4) 0.7894(5) 0.032 Uiso 1 1 d D . .


_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
Cl1 C5 1.7430(16) . ?
O1 C1 1.374(2) . ?
O1 C8 1.383(2) . ?
O2 C9 1.414(2) . ?
O2 H1 0.838(9) . ?
O3 N1 1.2215(18) . ?
O4 N1 1.2219(18) . ?
C1 C2 1.342(2) . ?
C1 C9 1.497(2) . ?
C2 C3 1.446(2) . ?
C2 H2A 0.9300 . ?
C3 C8 1.392(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.383(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.400(3) . ?
C6 C7 1.384(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.375(2) . ?
C7 H7A 0.9300 . ?
C9 C10 1.517(2) . ?
C9 H9A 0.9800 . ?
N1 C10 1.493(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
C1 O1 C8 105.26(12) . . ?
C9 O2 H1 106.1(14) . . ?
C2 C1 O1 112.91(14) . . ?
C2 C1 C9 133.16(15) . . ?
O1 C1 C9 113.88(13) . . ?
C1 C2 C3 105.91(15) . . ?
C1 C2 H2A 127.0 . . ?
C3 C2 H2A 127.0 . . ?
C8 C3 C4 119.21(14) . . ?
C8 C3 C2 105.71(14) . . ?
C4 C3 C2 135.08(16) . . ?
C5 C4 C3 116.96(16) . . ?
C5 C4 H4A 121.5 . . ?
C3 C4 H4A 121.5 . . ?
C4 C5 C6 122.84(15) . . ?
C4 C5 Cl1 118.89(13) . . ?
C6 C5 Cl1 118.27(12) . . ?
C7 C6 C5 120.27(15) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C8 C7 C6 116.54(16) . . ?
C8 C7 H7A 121.7 . . ?
C6 C7 H7A 121.7 . . ?
C7 C8 O1 125.64(16) . . ?
C7 C8 C3 124.16(16) . . ?
O1 C8 C3 110.20(13) . . ?
O2 C9 C1 107.73(13) . . ?
O2 C9 C10 111.85(12) . . ?
C1 C9 C10 110.50(13) . . ?
O2 C9 H9A 108.9 . . ?
C1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
O3 N1 O4 123.60(13) . . ?
O3 N1 C10 118.15(13) . . ?
O4 N1 C10 118.25(12) . . ?
N1 C10 C9 109.36(12) . . ?
N1 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
N1 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?

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
C8 O1 C1 C2 0.31(18) . . . . ?
C8 O1 C1 C9 -177.39(12) . . . . ?
O1 C1 C2 C3 -0.73(19) . . . . ?
C9 C1 C2 C3 176.39(16) . . . . ?
C1 C2 C3 C8 0.84(17) . . . . ?
C1 C2 C3 C4 -179.00(17) . . . . ?
C8 C3 C4 C5 -0.6(2) . . . . ?
C2 C3 C4 C5 179.28(16) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C3 C4 C5 Cl1 -178.82(11) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
Cl1 C5 C6 C7 178.61(13) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C6 C7 C8 O1 -179.24(14) . . . . ?
C6 C7 C8 C3 -0.1(2) . . . . ?
C1 O1 C8 C7 179.53(15) . . . . ?
C1 O1 C8 C3 0.26(16) . . . . ?
C4 C3 C8 C7 -0.1(2) . . . . ?
C2 C3 C8 C7 -179.96(16) . . . . ?
C4 C3 C8 O1 179.19(13) . . . . ?
C2 C3 C8 O1 -0.68(16) . . . . ?
C2 C1 C9 O2 -4.7(2) . . . . ?
O1 C1 C9 O2 172.45(12) . . . . ?
C2 C1 C9 C10 117.8(2) . . . . ?
O1 C1 C9 C10 -65.09(16) . . . . ?
O3 N1 C10 C9 128.85(16) . . . . ?
O4 N1 C10 C9 -51.12(18) . . . . ?
O2 C9 C10 N1 -69.77(16) . . . . ?
C1 C9 C10 N1 170.21(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        62.12
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc-Hexane'
_chemical_properties_physical    ', Heat-sensitive'
