#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/29/2232955.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_2232955
loop_
_publ_author_name
'Duo, De-Long'
'Ni, Cheng-Yan'
'Wen, Qing-Song'
_publ_section_title
;
 (2R,3R)-1-(4-Chlorophenyl)-2-[(S)-2-nitro-1-phenylethyl]-3-phenylpentan-1-one
;
_journal_coeditor_code           SU2340
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3495
_journal_paper_doi               10.1107/S1600536811050306
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C25 H24 Cl N O3'
_chemical_formula_moiety         'C25 H24 Cl N O3'
_chemical_formula_sum            'C25 H24 Cl N O3'
_chemical_formula_weight         421.90
_chemical_name_systematic
;
(2R,3R)-1-(4-Chlorophenyl)-2-[(S)-2-nitro-1-phenylethyl]-
3-phenylpentan-1-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.47000(10)
_cell_length_b                   13.1515(2)
_cell_length_c                   20.7060(2)
_cell_measurement_reflns_used    16354
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7588
_cell_measurement_theta_min      3.3577
_cell_volume                     2306.51(5)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Gemini S Ultra Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22729
_diffrn_reflns_theta_full        69.89
_diffrn_reflns_theta_max         69.89
_diffrn_reflns_theta_min         3.98
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  0.6353
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.246
_refine_ls_abs_structure_details 'Flack (1983), 1824 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.010(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0349
_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)+(0.0641P)²+0.1848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                4173
_reflns_number_total             4292
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2340.cif
_cod_data_source_block           I
_cod_database_code               2232955
_cod_database_fobs_code          2232955
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 x+1/2,-y+1/2,-z
4 -x,y+1/2,-z+1/2
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
_atom_site_symmetry_multiplicity
Cl Cl1 0.58917(6) 0.37368(4) 0.50249(2) 0.08473(17) Uani d . 1 1
O O1 0.50133(14) 0.00173(10) 0.28825(7) 0.0700(3) Uani d . 1 1
O O2 0.7782(3) -0.30696(14) 0.25735(12) 0.1277(8) Uani d . 1 1
O O3 0.9069(3) -0.23945(18) 0.18103(18) 0.1769(14) Uani d . 1 1
N N1 0.8118(2) -0.23648(13) 0.22259(12) 0.0826(5) Uani d . 1 1
C C1 0.5978(2) 0.28418(13) 0.44074(8) 0.0595(4) Uani d . 1 1
C C2 0.46287(19) 0.23354(13) 0.42310(7) 0.0565(4) Uani d . 1 1
H H2 0.3673 0.2482 0.4431 0.068 Uiso calc R 1 1
C C3 0.47066(18) 0.16045(12) 0.37513(7) 0.0509(3) Uani d . 1 1
H H3 0.3801 0.1251 0.3634 0.061 Uiso calc R 1 1
C C4 0.61302(18) 0.13951(11) 0.34438(7) 0.0495(3) Uani d . 1 1
C C5 0.7473(2) 0.19166(15) 0.36286(9) 0.0646(4) Uani d . 1 1
H H5 0.8430 0.1778 0.3427 0.078 Uiso calc R 1 1
C C6 0.7404(2) 0.26467(16) 0.41126(9) 0.0697(5) Uani d . 1 1
H H6 0.8308 0.2999 0.4236 0.084 Uiso calc R 1 1
C C7 0.61293(18) 0.05938(12) 0.29275(7) 0.0519(3) Uani d . 1 1
C C8 0.74862(17) 0.05223(12) 0.24430(7) 0.0499(3) Uani d . 1 1
H H8 0.8271 0.1037 0.2561 0.060 Uiso calc R 1 1
C C9 0.68287(19) 0.08030(12) 0.17641(8) 0.0544(3) Uani d . 1 1
H H9 0.5912 0.0368 0.1681 0.065 Uiso calc R 1 1
C C10 0.80251(19) 0.06096(12) 0.12331(7) 0.0528(3) Uani d . 1 1
C C11 0.7672(2) -0.00341(15) 0.07273(8) 0.0664(4) Uani d . 1 1
H H11 0.6694 -0.0355 0.0720 0.080 Uiso calc R 1 1
C C12 0.8725(3) -0.02151(18) 0.02330(10) 0.0846(6) Uani d . 1 1
H H12 0.8454 -0.0651 -0.0103 0.102 Uiso calc R 1 1
C C13 1.0170(3) 0.0248(2) 0.02388(11) 0.0923(7) Uani d . 1 1
H H13 1.0893 0.0123 -0.0090 0.111 Uiso calc R 1 1
C C14 1.0545(3) 0.0903(2) 0.07361(12) 0.0973(7) Uani d . 1 1
H H14 1.1523 0.1224 0.0740 0.117 Uiso calc R 1 1
C C15 0.9477(2) 0.10866(18) 0.12305(10) 0.0763(5) Uani d . 1 1
H H15 0.9740 0.1533 0.1562 0.092 Uiso calc R 1 1
C C16 0.6259(3) 0.19137(16) 0.17528(9) 0.0745(5) Uani d . 1 1
H H16A 0.5516 0.2017 0.2104 0.089 Uiso calc R 1 1
H H16B 0.7154 0.2359 0.1826 0.089 Uiso calc R 1 1
C C17 0.5474(3) 0.2207(2) 0.11228(12) 0.0983(7) Uani d . 1 1
H H17A 0.4587 0.1769 0.1046 0.148 Uiso calc R 1 1
H H17B 0.6218 0.2139 0.0776 0.148 Uiso calc R 1 1
H H17C 0.5119 0.2899 0.1147 0.148 Uiso calc R 1 1
C C18 0.83087(17) -0.05335(12) 0.24718(7) 0.0512(3) Uani d . 1 1
H H18 0.9132 -0.0522 0.2139 0.061 Uiso calc R 1 1
C C19 0.91484(19) -0.07057(11) 0.31084(7) 0.0529(3) Uani d . 1 1
C C20 1.0760(2) -0.05423(14) 0.31501(9) 0.0652(4) Uani d . 1 1
H H20 1.1310 -0.0316 0.2789 0.078 Uiso calc R 1 1
C C21 1.1568(3) -0.07107(16) 0.37241(12) 0.0809(6) Uani d . 1 1
H H21 1.2651 -0.0595 0.3743 0.097 Uiso calc R 1 1
C C22 1.0794(3) -0.10408(16) 0.42545(10) 0.0813(6) Uani d . 1 1
H H22 1.1345 -0.1166 0.4635 0.098 Uiso calc R 1 1
C C23 0.9185(3) -0.11912(17) 0.42302(9) 0.0825(6) Uani d . 1 1
H H23 0.8646 -0.1406 0.4597 0.099 Uiso calc R 1 1
C C24 0.8368(2) -0.10225(17) 0.36589(9) 0.0702(5) Uani d . 1 1
H H24 0.7282 -0.1124 0.3647 0.084 Uiso calc R 1 1
C C25 0.7198(2) -0.14079(12) 0.22928(9) 0.0595(4) Uani d . 1 1
H H25A 0.6401 -0.1489 0.2626 0.071 Uiso calc R 1 1
H H25B 0.6667 -0.1255 0.1889 0.071 Uiso calc R 1 1
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'
Cl Cl 0.3639 0.7018 '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
O3 N1 O2 124.8(2)
O3 N1 C25 117.0(2)
O2 N1 C25 118.1(2)
C2 C1 C6 121.45(14)
C2 C1 Cl1 119.29(12)
C6 C1 Cl1 119.25(14)
C1 C2 C3 119.24(14)
C1 C2 H2 120.4
C3 C2 H2 120.4
C2 C3 C4 120.49(14)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 119.23(13)
C5 C4 C7 123.09(13)
C3 C4 C7 117.67(13)
C4 C5 C6 120.54(16)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 119.03(17)
C1 C6 H6 120.5
C5 C6 H6 120.5
O1 C7 C4 119.54(13)
O1 C7 C8 119.74(13)
C4 C7 C8 120.68(13)
C7 C8 C18 111.51(12)
C7 C8 C9 108.01(12)
C18 C8 C9 114.01(12)
C7 C8 H8 107.7
C18 C8 H8 107.7
C9 C8 H8 107.7
C10 C9 C16 110.97(14)
C10 C9 C8 112.08(12)
C16 C9 C8 110.56(14)
C10 C9 H9 107.7
C16 C9 H9 107.7
C8 C9 H9 107.7
C11 C10 C15 117.99(16)
C11 C10 C9 120.55(15)
C15 C10 C9 121.44(15)
C12 C11 C10 121.95(19)
C12 C11 H11 119.0
C10 C11 H11 119.0
C13 C12 C11 119.7(2)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C14 119.41(19)
C12 C13 H13 120.3
C14 C13 H13 120.3
C13 C14 C15 120.6(2)
C13 C14 H14 119.7
C15 C14 H14 119.7
C10 C15 C14 120.29(19)
C10 C15 H15 119.9
C14 C15 H15 119.9
C17 C16 C9 113.12(18)
C17 C16 H16A 109.0
C9 C16 H16A 109.0
C17 C16 H16B 109.0
C9 C16 H16B 109.0
H16A C16 H16B 107.8
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 C25 112.75(14)
C19 C18 C8 112.17(12)
C25 C18 C8 112.71(13)
C19 C18 H18 106.2
C25 C18 H18 106.2
C8 C18 H18 106.2
C24 C19 C20 117.82(16)
C24 C19 C18 122.57(15)
C20 C19 C18 119.61(15)
C19 C20 C21 120.96(19)
C19 C20 H20 119.5
C21 C20 H20 119.5
C22 C21 C20 120.5(2)
C22 C21 H21 119.7
C20 C21 H21 119.7
C21 C22 C23 119.76(19)
C21 C22 H22 120.1
C23 C22 H22 120.1
C22 C23 C24 120.1(2)
C22 C23 H23 120.0
C24 C23 H23 120.0
C19 C24 C23 120.83(19)
C19 C24 H24 119.6
C23 C24 H24 119.6
N1 C25 C18 109.64(14)
N1 C25 H25A 109.7
C18 C25 H25A 109.7
N1 C25 H25B 109.7
C18 C25 H25B 109.7
H25A C25 H25B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7393(15)
O1 C7 1.2153(19)
O2 N1 1.208(3)
O3 N1 1.180(3)
N1 C25 1.487(2)
C1 C2 1.372(3)
C1 C6 1.378(3)
C2 C3 1.384(2)
C2 H2 0.9300
C3 C4 1.391(2)
C3 H3 0.9300
C4 C5 1.382(2)
C4 C7 1.501(2)
C5 C6 1.389(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.5285(19)
C8 C18 1.555(2)
C8 C9 1.556(2)
C8 H8 0.9800
C9 C10 1.517(2)
C9 C16 1.539(2)
C9 H9 0.9800
C10 C11 1.379(2)
C10 C15 1.381(2)
C11 C12 1.378(3)
C11 H11 0.9300
C12 C13 1.367(4)
C12 H12 0.9300
C13 C14 1.379(4)
C13 H13 0.9300
C14 C15 1.387(3)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.514(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.515(2)
C18 C25 1.531(2)
C18 H18 0.9800
C19 C24 1.382(2)
C19 C20 1.385(2)
C20 C21 1.389(3)
C20 H20 0.9300
C21 C22 1.351(3)
C21 H21 0.9300
C22 C23 1.378(4)
C22 H22 0.9300
C23 C24 1.388(3)
C23 H23 0.9300
C24 H24 0.9300
C25 H25A 0.9700
C25 H25B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5 O3 4_755 0.93 2.43 3.198(5) 140 yes
C12 H12 CgA 2_654 0.93 2.82 3.691(4) 157 yes
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
C6 C1 C2 C3 0.7(3)
Cl1 C1 C2 C3 -178.32(12)
C1 C2 C3 C4 -1.0(2)
C2 C3 C4 C5 0.8(2)
C2 C3 C4 C7 -179.95(14)
C3 C4 C5 C6 -0.4(3)
C7 C4 C5 C6 -179.60(17)
C2 C1 C6 C5 -0.3(3)
Cl1 C1 C6 C5 178.72(16)
C4 C5 C6 C1 0.2(3)
C5 C4 C7 O1 164.28(18)
C3 C4 C7 O1 -14.9(2)
C5 C4 C7 C8 -18.1(2)
C3 C4 C7 C8 162.74(14)
O1 C7 C8 C18 -61.3(2)
C4 C7 C8 C18 121.03(15)
O1 C7 C8 C9 64.69(19)
C4 C7 C8 C9 -112.95(15)
C7 C8 C9 C10 -171.81(13)
C18 C8 C9 C10 -47.28(18)
C7 C8 C9 C16 63.81(17)
C18 C8 C9 C16 -171.65(14)
C16 C9 C10 C11 -113.53(19)
C8 C9 C10 C11 122.32(17)
C16 C9 C10 C15 64.8(2)
C8 C9 C10 C15 -59.3(2)
C15 C10 C11 C12 0.7(3)
C9 C10 C11 C12 179.12(18)
C10 C11 C12 C13 0.3(4)
C11 C12 C13 C14 -0.9(4)
C12 C13 C14 C15 0.5(4)
C11 C10 C15 C14 -1.0(3)
C9 C10 C15 C14 -179.4(2)
C13 C14 C15 C10 0.4(4)
C10 C9 C16 C17 60.0(2)
C8 C9 C16 C17 -174.97(18)
C7 C8 C18 C19 -66.22(16)
C9 C8 C18 C19 171.13(12)
C7 C8 C18 C25 62.33(17)
C9 C8 C18 C25 -60.31(17)
C25 C18 C19 C24 -47.1(2)
C8 C18 C19 C24 81.41(19)
C25 C18 C19 C20 132.96(16)
C8 C18 C19 C20 -98.51(16)
C24 C19 C20 C21 1.2(3)
C18 C19 C20 C21 -178.86(17)
C19 C20 C21 C22 0.1(3)
C20 C21 C22 C23 -1.4(3)
C21 C22 C23 C24 1.2(3)
C20 C19 C24 C23 -1.4(3)
C18 C19 C24 C23 178.72(17)
C22 C23 C24 C19 0.2(3)
O3 N1 C25 C18 -63.7(3)
O2 N1 C25 C18 120.2(2)
C19 C18 C25 N1 -60.96(19)
C8 C18 C25 N1 170.79(16)
