#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230472.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_2230472
loop_
_publ_author_name
'Song, Xiu-Mei'
'Wang, Ning'
'Wang, Zhao-Yang'
'Feng, Zong-Cai'
_publ_section_title
;
 3-Chloro-4-dimethylamino-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one
;
_journal_coeditor_code           SI2350
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1485
_journal_page_last               o1486
_journal_paper_doi               10.1107/S1600536811015583
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H26 Cl N O3'
_chemical_formula_moiety         'C16 H26 Cl N O3'
_chemical_formula_sum            'C16 H26 Cl N O3'
_chemical_formula_weight         315.83
_chemical_name_systematic
;
3-Chloro-4-dimethylamino-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                   7.5438(5)
_cell_length_b                   8.1631(5)
_cell_length_c                   28.5953(17)
_cell_measurement_reflns_used    3099
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.54
_cell_measurement_theta_min      2.79
_cell_volume                     1760.92(19)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9112
_diffrn_reflns_theta_full        25.18
_diffrn_reflns_theta_max         25.18
_diffrn_reflns_theta_min         1.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.9498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.138
_refine_ls_abs_structure_details 'Flack (1983), 1066 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0468
_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)+(0.0550P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                1951
_reflns_number_total             2922
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2350.cif
_cod_data_source_block           I
_cod_database_code               2230472
_cod_database_fobs_code          2230472
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4580(5) 0.8674(4) 0.45480(10) 0.0785(11) Uani d . 1 1 . .
H H1A 0.3934 0.7827 0.4714 0.094 Uiso calc R 1 1 . .
H H1B 0.5740 0.8773 0.4691 0.094 Uiso calc R 1 1 . .
C C2 0.4806(4) 0.8152(4) 0.40327(9) 0.0628(9) Uani d . 1 1 . .
H H2 0.5491 0.9020 0.3880 0.075 Uiso calc R 1 1 . .
C C3 0.2995(4) 0.8133(3) 0.37990(9) 0.0525(8) Uani d . 1 1 . .
H H3 0.2272 0.7270 0.3942 0.063 Uiso calc R 1 1 . .
C C4 0.2051(5) 0.9754(3) 0.38525(9) 0.0701(10) Uani d . 1 1 . .
H H4A 0.0895 0.9685 0.3705 0.084 Uiso calc R 1 1 . .
H H4B 0.2724 1.0599 0.3693 0.084 Uiso calc R 1 1 . .
C C5 0.1815(6) 1.0237(4) 0.43669(11) 0.0804(11) Uani d . 1 1 . .
H H5 0.1112 0.9379 0.4519 0.096 Uiso calc R 1 1 . .
C C6 0.3610(7) 1.0271(4) 0.45991(11) 0.0893(12) Uani d . 1 1 . .
H H6A 0.4316 1.1140 0.4462 0.107 Uiso calc R 1 1 . .
H H6B 0.3462 1.0514 0.4929 0.107 Uiso calc R 1 1 . .
C C7 0.0799(7) 1.1841(5) 0.44127(12) 0.1207(16) Uani d . 1 1 . .
H H7A 0.0713 1.2137 0.4737 0.181 Uiso calc R 1 1 . .
H H7B -0.0369 1.1710 0.4285 0.181 Uiso calc R 1 1 . .
H H7C 0.1413 1.2688 0.4245 0.181 Uiso calc R 1 1 . .
C C8 0.5869(5) 0.6562(4) 0.39706(11) 0.0718(10) Uani d . 1 1 . .
H H8 0.5775 0.6257 0.3640 0.086 Uiso calc R 1 1 . .
C C9 0.5161(5) 0.5122(4) 0.42518(12) 0.0989(14) Uani d . 1 1 . .
H H9A 0.5293 0.5345 0.4580 0.148 Uiso calc R 1 1 . .
H H9B 0.5814 0.4151 0.4173 0.148 Uiso calc R 1 1 . .
H H9C 0.3930 0.4960 0.4181 0.148 Uiso calc R 1 1 . .
C C10 0.7855(5) 0.6823(6) 0.40726(13) 0.1098(14) Uani d . 1 1 . .
H H10A 0.8276 0.7752 0.3899 0.165 Uiso calc R 1 1 . .
H H10B 0.8507 0.5865 0.3981 0.165 Uiso calc R 1 1 . .
H H10C 0.8019 0.7016 0.4401 0.165 Uiso calc R 1 1 . .
C C11 0.2476(5) 0.4116(4) 0.31317(11) 0.0793(11) Uani d . 1 1 . .
H H11A 0.3620 0.3966 0.3272 0.119 Uiso calc R 1 1 . .
H H11B 0.1923 0.3069 0.3087 0.119 Uiso calc R 1 1 . .
H H11C 0.1751 0.4777 0.3333 0.119 Uiso calc R 1 1 . .
C C12 0.3298(6) 0.3891(4) 0.23027(11) 0.0928(12) Uani d . 1 1 . .
H H12A 0.2355 0.3726 0.2082 0.139 Uiso calc R 1 1 . .
H H12B 0.3670 0.2853 0.2426 0.139 Uiso calc R 1 1 . .
H H12C 0.4280 0.4411 0.2149 0.139 Uiso calc R 1 1 . .
C C13 0.2303(4) 0.6503(3) 0.26159(9) 0.0495(7) Uani d . 1 1 . .
C C14 0.2256(4) 0.7458(3) 0.22286(9) 0.0530(8) Uani d . 1 1 . .
C C15 0.1758(4) 0.9092(4) 0.23489(11) 0.0588(8) Uani d . 1 1 . .
C C16 0.1844(4) 0.7605(3) 0.30258(10) 0.0529(8) Uani d . 1 1 . .
H H16 0.0818 0.7180 0.3198 0.063 Uiso calc R 1 1 . .
Cl Cl1 0.26385(14) 0.70164(12) 0.16516(3) 0.0940(4) Uani d . 1 1 . .
N N1 0.2678(3) 0.4928(3) 0.26825(8) 0.0609(7) Uani d . 1 1 . .
O O1 0.3317(3) 0.7719(2) 0.33142(6) 0.0524(5) Uani d . 1 1 . .
O O2 0.1456(3) 0.9169(2) 0.28218(6) 0.0627(6) Uani d . 1 1 . .
O O3 0.1584(3) 1.0295(3) 0.21086(7) 0.0817(7) Uani d . 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 0.0033 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
C6 C1 C2 . . 112.7(3) ?
C6 C1 H1A . . 109.0 ?
C2 C1 H1A . . 109.0 ?
C6 C1 H1B . . 109.0 ?
C2 C1 H1B . . 109.0 ?
H1A C1 H1B . . 107.8 ?
C3 C2 C8 . . 114.2(3) ?
C3 C2 C1 . . 108.8(3) ?
C8 C2 C1 . . 113.7(3) ?
C3 C2 H2 . . 106.5 ?
C8 C2 H2 . . 106.5 ?
C1 C2 H2 . . 106.5 ?
O1 C3 C4 . . 112.3(2) ?
O1 C3 C2 . . 105.8(2) ?
C4 C3 C2 . . 111.7(3) ?
O1 C3 H3 . . 109.0 ?
C4 C3 H3 . . 109.0 ?
C2 C3 H3 . . 109.0 ?
C3 C4 C5 . . 112.1(2) ?
C3 C4 H4A . . 109.2 ?
C5 C4 H4A . . 109.2 ?
C3 C4 H4B . . 109.2 ?
C5 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
C6 C5 C7 . . 113.5(3) ?
C6 C5 C4 . . 108.8(3) ?
C7 C5 C4 . . 111.2(3) ?
C6 C5 H5 . . 107.7 ?
C7 C5 H5 . . 107.7 ?
C4 C5 H5 . . 107.7 ?
C1 C6 C5 . . 112.2(3) ?
C1 C6 H6A . . 109.2 ?
C5 C6 H6A . . 109.2 ?
C1 C6 H6B . . 109.2 ?
C5 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C2 . . 114.1(3) ?
C9 C8 C10 . . 110.4(3) ?
C2 C8 C10 . . 111.6(3) ?
C9 C8 H8 . . 106.8 ?
C2 C8 H8 . . 106.8 ?
C10 C8 H8 . . 106.8 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N1 C11 H11A . . 109.5 ?
N1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 C14 . . 132.7(3) ?
N1 C13 C16 . . 120.7(2) ?
C14 C13 C16 . . 106.5(2) ?
C13 C14 C15 . . 110.3(2) ?
C13 C14 Cl1 . . 131.5(2) ?
C15 C14 Cl1 . . 118.2(2) ?
O3 C15 O2 . . 120.4(3) ?
O3 C15 C14 . . 130.7(3) ?
O2 C15 C14 . . 108.9(2) ?
O1 C16 O2 . . 110.2(2) ?
O1 C16 C13 . . 108.4(2) ?
O2 C16 C13 . . 105.1(2) ?
O1 C16 H16 . . 111.0 ?
O2 C16 H16 . . 111.0 ?
C13 C16 H16 . . 111.0 ?
C13 N1 C11 . . 123.0(2) ?
C13 N1 C12 . . 121.6(3) ?
C11 N1 C12 . . 115.4(2) ?
C16 O1 C3 . . 116.8(2) ?
C15 O2 C16 . . 109.0(2) ?
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
C1 C6 . 1.502(5) ?
C1 C2 . 1.544(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.521(4) ?
C2 C8 . 1.536(5) ?
C2 H2 . 0.9800 ?
C3 O1 . 1.447(3) ?
C3 C4 . 1.511(4) ?
C3 H3 . 0.9800 ?
C4 C5 . 1.533(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.509(6) ?
C5 C7 . 1.523(5) ?
C5 H5 . 0.9800 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.521(4) ?
C8 C10 . 1.541(5) ?
C8 H8 . 0.9800 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 N1 . 1.453(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 N1 . 1.454(4) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 N1 . 1.331(3) ?
C13 C14 . 1.354(3) ?
C13 C16 . 1.518(4) ?
C14 C15 . 1.428(4) ?
C14 Cl1 . 1.713(3) ?
C15 O3 . 1.205(3) ?
C15 O2 . 1.373(3) ?
C16 O1 . 1.387(3) ?
C16 O2 . 1.434(3) ?
C16 H16 . 0.9800 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656736
