#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/89/2228914.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_2228914
loop_
_publ_author_name
'Fu, Jian-Hua'
'Wang, Zhao-Yang'
'Xue, Fu-Ling'
'Huo, Jing-Pei'
_publ_section_title
;
 (5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one
;
_journal_coeditor_code           XU5106
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o73
_journal_paper_doi               10.1107/S1600536810051226
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H26 Cl N O3'
_chemical_formula_moiety         'C18 H26 Cl N O3'
_chemical_formula_sum            'C18 H26 Cl N O3'
_chemical_formula_weight         339.85
_chemical_name_systematic
;
(5S)-3-Chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)-
5-[(1R,2S,5R)-2-isopropyl-5-
methylcyclohexyloxy]furan-2(5H)-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                   7.192(2)
_cell_length_b                   9.622(3)
_cell_length_c                   27.534(9)
_cell_measurement_reflns_used    1222
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      17.50
_cell_measurement_theta_min      2.24
_cell_volume                     1905.4(10)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (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  'Bruker APEXII area-detector'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9627
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.135
_refine_ls_abs_structure_details 'Flack (1983), 1398 Friedel pairs'
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1291
_reflns_number_gt                1708
_reflns_number_total             3363
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5106.cif
_cod_data_source_block           I
_cod_database_code               2228914
_cod_database_fobs_code          2228914
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'
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.78504(18) 0.24214(12) 0.34421(3) 0.1169(5) Uani d . 1 . .
C C3 0.7443(5) 0.2768(4) 0.24451(11) 0.0695(9) Uani d . 1 . .
C C4 0.7076(5) 0.1802(4) 0.20226(12) 0.0744(10) Uani d . 1 . .
H H4 0.5952 0.2084 0.1847 0.089 Uiso calc R 1 . .
C C5 0.8243(6) 0.1400(4) 0.12119(10) 0.0775(11) Uani d . 1 . .
H H5 0.7375 0.2071 0.1070 0.093 Uiso calc R 1 . .
C C1 0.7075(6) 0.0576(5) 0.27315(13) 0.0840(11) Uani d . 1 . .
C C2 0.7477(5) 0.1979(4) 0.28492(11) 0.0773(10) Uani d . 1 . .
C C6 1.0128(6) 0.1530(5) 0.09539(12) 0.0901(13) Uani d . 1 . .
H H6 1.0961 0.0856 0.1108 0.108 Uiso calc R 1 . .
C C10 0.7420(7) -0.0036(4) 0.11707(11) 0.1015(13) Uani d . 1 . .
H H10A 0.6212 -0.0050 0.1327 0.122 Uiso calc R 1 . .
H H10B 0.8216 -0.0695 0.1338 0.122 Uiso calc R 1 . .
C C7 0.9896(8) 0.1062(5) 0.04242(13) 0.1185(18) Uani d . 1 . .
H H7A 0.9093 0.1714 0.0256 0.142 Uiso calc R 1 . .
H H7B 1.1099 0.1076 0.0265 0.142 Uiso calc R 1 . .
C C11 1.1050(6) 0.2946(6) 0.10072(14) 0.1047(15) Uani d . 1 . .
H H11 1.0932 0.3206 0.1350 0.126 Uiso calc R 1 . .
C C9 0.7204(10) -0.0480(5) 0.06354(14) 0.1288(18) Uani d . 1 . .
H H9 0.6340 0.0161 0.0476 0.155 Uiso calc R 1 . .
C C8 0.9082(10) -0.0374(7) 0.03860(16) 0.140(2) Uani d . 1 . .
H H8A 0.9932 -0.1035 0.0532 0.168 Uiso calc R 1 . .
H H8B 0.8942 -0.0616 0.0046 0.168 Uiso calc R 1 . .
C C14 1.0115(8) 0.4096(5) 0.07156(16) 0.140(2) Uani d . 1 . .
H H14A 1.0309 0.3936 0.0375 0.210 Uiso calc R 1 . .
H H14B 1.0641 0.4978 0.0804 0.210 Uiso calc R 1 . .
H H14C 0.8805 0.4100 0.0783 0.210 Uiso calc R 1 . .
C C13 1.3143(7) 0.2870(7) 0.08997(15) 0.160(2) Uani d . 1 . .
H H13A 1.3696 0.2151 0.1093 0.241 Uiso calc R 1 . .
H H13B 1.3712 0.3746 0.0977 0.241 Uiso calc R 1 . .
H H13C 1.3329 0.2667 0.0562 0.241 Uiso calc R 1 . .
C C12 0.6404(13) -0.1951(7) 0.06041(19) 0.217(4) Uani d . 1 . .
H H12A 0.6598 -0.2313 0.0283 0.326 Uiso calc R 1 . .
H H12B 0.5096 -0.1925 0.0673 0.326 Uiso calc R 1 . .
H H12C 0.7017 -0.2537 0.0836 0.326 Uiso calc R 1 . .
C C18 0.7548(7) 0.4780(4) 0.18901(13) 0.0971(12) Uani d . 1 . .
H H18A 0.6422 0.4507 0.1721 0.117 Uiso calc R 1 . .
H H18B 0.8618 0.4566 0.1689 0.117 Uiso calc R 1 . .
C C15 0.7871(6) 0.5142(4) 0.27610(13) 0.0967(13) Uani d . 1 . .
H H15A 0.6884 0.5045 0.2999 0.116 Uiso calc R 1 . .
H H15B 0.9064 0.5059 0.2923 0.116 Uiso calc R 1 . .
C C17 0.7505(7) 0.6280(4) 0.20278(19) 0.1103(14) Uani d . 1 . .
H H17 0.7344 0.7001 0.1807 0.132 Uiso calc R 1 . .
C C16 0.7720(7) 0.6461(5) 0.2495(2) 0.1092(14) Uani d . 1 . .
H H16 0.7772 0.7329 0.2643 0.131 Uiso calc R 1 . .
N N1 0.7681(5) 0.4111(3) 0.23671(9) 0.0791(9) Uani d . 1 . .
O O3 0.8607(3) 0.1789(2) 0.17127(7) 0.0767(7) Uani d . 1 . .
O O1 0.6832(4) 0.0450(2) 0.22383(8) 0.0845(8) Uani d . 1 . .
O O2 0.6958(5) -0.0440(3) 0.29863(9) 0.1111(10) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C3 C2 . . 133.1(3) ?
N1 C3 C4 . . 119.9(3) ?
C2 C3 C4 . . 107.0(3) ?
O3 C4 O1 . . 109.9(3) ?
O3 C4 C3 . . 109.8(3) ?
O1 C4 C3 . . 105.0(3) ?
O3 C4 H4 . . 110.7 ?
O1 C4 H4 . . 110.7 ?
C3 C4 H4 . . 110.7 ?
O3 C5 C10 . . 112.2(3) ?
O3 C5 C6 . . 105.0(3) ?
C10 C5 C6 . . 112.8(4) ?
O3 C5 H5 . . 108.9 ?
C10 C5 H5 . . 108.9 ?
C6 C5 H5 . . 108.9 ?
O2 C1 O1 . . 119.6(4) ?
O2 C1 C2 . . 130.8(3) ?
O1 C1 C2 . . 109.6(3) ?
C3 C2 C1 . . 110.1(3) ?
C3 C2 Cl1 . . 130.7(3) ?
C1 C2 Cl1 . . 119.2(3) ?
C11 C6 C7 . . 113.7(4) ?
C11 C6 C5 . . 114.4(3) ?
C7 C6 C5 . . 108.6(4) ?
C11 C6 H6 . . 106.5 ?
C7 C6 H6 . . 106.5 ?
C5 C6 H6 . . 106.5 ?
C5 C10 C9 . . 111.4(3) ?
C5 C10 H10A . . 109.3 ?
C9 C10 H10A . . 109.3 ?
C5 C10 H10B . . 109.3 ?
C9 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
C8 C7 C6 . . 112.2(4) ?
C8 C7 H7A . . 109.2 ?
C6 C7 H7A . . 109.2 ?
C8 C7 H7B . . 109.2 ?
C6 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
C6 C11 C14 . . 114.0(4) ?
C6 C11 C13 . . 111.5(5) ?
C14 C11 C13 . . 111.4(5) ?
C6 C11 H11 . . 106.5 ?
C14 C11 H11 . . 106.5 ?
C13 C11 H11 . . 106.5 ?
C8 C9 C12 . . 111.8(5) ?
C8 C9 C10 . . 108.9(4) ?
C12 C9 C10 . . 110.4(4) ?
C8 C9 H9 . . 108.6 ?
C12 C9 H9 . . 108.6 ?
C10 C9 H9 . . 108.6 ?
C7 C8 C9 . . 112.1(5) ?
C7 C8 H8A . . 109.2 ?
C9 C8 H8A . . 109.2 ?
C7 C8 H8B . . 109.2 ?
C9 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C18 C17 . . 101.4(3) ?
N1 C18 H18A . . 111.5 ?
C17 C18 H18A . . 111.5 ?
N1 C18 H18B . . 111.5 ?
C17 C18 H18B . . 111.5 ?
H18A C18 H18B . . 109.3 ?
C16 C15 N1 . . 102.0(3) ?
C16 C15 H15A . . 111.4 ?
N1 C15 H15A . . 111.4 ?
C16 C15 H15B . . 111.4 ?
N1 C15 H15B . . 111.4 ?
H15A C15 H15B . . 109.2 ?
C16 C17 C18 . . 112.1(4) ?
C16 C17 H17 . . 123.9 ?
C18 C17 H17 . . 123.9 ?
C17 C16 C15 . . 112.5(4) ?
C17 C16 H16 . . 123.7 ?
C15 C16 H16 . . 123.7 ?
C3 N1 C18 . . 124.5(3) ?
C3 N1 C15 . . 123.3(3) ?
C18 N1 C15 . . 111.7(3) ?
C4 O3 C5 . . 116.2(3) ?
C1 O1 C4 . . 108.2(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . 1.709(3) ?
C3 N1 . 1.321(4) ?
C3 C2 . 1.347(4) ?
C3 C4 . 1.512(4) ?
C4 O3 . 1.393(4) ?
C4 O1 . 1.441(4) ?
C4 H4 . 0.9800 ?
C5 O3 . 1.453(3) ?
C5 C10 . 1.507(5) ?
C5 C6 . 1.536(5) ?
C5 H5 . 0.9800 ?
C1 O2 . 1.206(4) ?
C1 O1 . 1.375(4) ?
C1 C2 . 1.418(5) ?
C6 C11 . 1.522(6) ?
C6 C7 . 1.535(5) ?
C6 H6 . 0.9800 ?
C10 C9 . 1.542(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C7 C8 . 1.504(6) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C11 C14 . 1.524(6) ?
C11 C13 . 1.535(6) ?
C11 H11 . 0.9800 ?
C9 C8 . 1.518(7) ?
C9 C12 . 1.530(7) ?
C9 H9 . 0.9800 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C18 N1 . 1.466(4) ?
C18 C17 . 1.492(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C15 C16 . 1.469(6) ?
C15 N1 . 1.476(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C17 C16 . 1.308(5) ?
C17 H17 . 0.9300 ?
C16 H16 . 0.9300 ?
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
C16 H16 O2 1_565 0.93 2.42 3.320(6) 164
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656443
