#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:29:22 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193888 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/54/7155462.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_7155462
loop_
_publ_author_name
'Chen, Wei'
'Zhou, Zhao-Hui'
'Chen, Hong-Bin'
_publ_section_title
;
 Efficient synthesis of chiral benzofuryl β-amino alcohols via a
 catalytic asymmetric Henry reaction.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1530
_journal_page_last               1536
_journal_paper_doi               10.1039/c6ob02569b
_journal_volume                  15
_journal_year                    2017
_chemical_formula_sum            'C10 H8 Cl N O4'
_chemical_formula_weight         241.62
_chemical_name_common            'Chloride substitute'
_chemical_name_systematic        (S)-1-(5-Chlorobenzofuran-2-yl)-2-nitroethanol
_chemical_properties_physical    ', Heat-sensitive'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-01-17 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5571(2)
_cell_length_b                   5.6305(2)
_cell_length_c                   32.3624(10)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      36
_cell_measurement_theta_min      34
_cell_volume                     1012.60(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Gemini Oxford Diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11073
_diffrn_reflns_theta_full        62.12
_diffrn_reflns_theta_max         62.12
_diffrn_reflns_theta_min         5.47
_exptl_absorpt_coefficient_mu    3.371
_exptl_absorpt_correction_T_max  0.7742
_exptl_absorpt_correction_T_min  0.5521
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc-Hexane'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1590
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0378P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0549
_reflns_number_gt                1505
_reflns_number_total             1590
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02569b2.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155461--7155462.cif.
;
_cod_database_code               7155462
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
