#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/77/2217720.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_2217720
loop_
_publ_author_name
'Tao, Xiao'
'Zhang, Xiao-Qing'
'Yuan, Lin'
'Wang, Jin-Tang'
_publ_section_title
;
 N,N-Dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine
;
_journal_coeditor_code           BH2157
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o553
_journal_paper_doi               10.1107/S1600536808003255
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C19 H21 N O S'
_chemical_formula_moiety         'C19 H21 N O S'
_chemical_formula_sum            'C19 H21 N O S'
_chemical_formula_weight         311.43
_chemical_melting_point          .386E-305
_chemical_name_systematic
;
N,N-Dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.53(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6140(19)
_cell_length_b                   18.578(4)
_cell_length_c                   9.905(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1712.5(7)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1981)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1981)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3550
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9277
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.317
_refine_ls_extinction_coef       0.094(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0699
_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)+(0.08P)²+0.85P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1942
_reflns_number_gt                2009
_reflns_number_total             3352
_reflns_threshold_expression     I>2s(I)
_cod_data_source_file            bh2157.cif
_cod_data_source_block           I
_cod_original_cell_volume        1712.5(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2217720
_cod_database_fobs_code          2217720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S S 0.03342(12) 0.25309(6) 0.17997(10) 0.0561(3) Uani d . 1
O O 0.1693(2) 0.34125(12) 0.0007(2) 0.0445(6) Uani d . 1
N N -0.1370(3) 0.47356(16) -0.2560(3) 0.0517(8) Uani d . 1
C C1 -0.2401(5) 0.4470(2) -0.3807(5) 0.0777(14) Uani d . 1
H H1A -0.2777 0.4015 -0.3607 0.117 Uiso calc R 1
H H1B -0.1929 0.4412 -0.4547 0.117 Uiso calc R 1
H H1C -0.3173 0.4809 -0.4086 0.117 Uiso calc R 1
C C2 -0.0803(5) 0.5421(2) -0.2843(5) 0.0753(13) Uani d . 1
H H2A -0.0133 0.5593 -0.2016 0.113 Uiso calc R 1
H H2B -0.1575 0.5760 -0.3123 0.113 Uiso calc R 1
H H2C -0.0322 0.5367 -0.3577 0.113 Uiso calc R 1
C C3 -0.0227(4) 0.4218(2) -0.2029(4) 0.0517(10) Uani d . 1
H H3A 0.0559 0.4461 -0.1383 0.062 Uiso calc R 1
H H3B 0.0131 0.4041 -0.2800 0.062 Uiso calc R 1
C C4 -0.0708(4) 0.3584(2) -0.1295(4) 0.0506(10) Uani d . 1
H H4A -0.1016 0.3758 -0.0493 0.061 Uiso calc R 1
H H4B -0.1527 0.3357 -0.1924 0.061 Uiso calc R 1
C C5 0.0463(4) 0.30309(19) -0.0816(4) 0.0439(9) Uani d . 1
H H5A 0.0711 0.2822 -0.1634 0.053 Uiso calc R 1
C C6 0.0029(4) 0.24339(18) 0.0033(4) 0.0406(8) Uani d . 1
C C7 -0.0719(4) 0.17959(18) -0.0465(4) 0.043 Uani d . 1
H H7A -0.0997 0.1649 -0.1392 0.052 Uiso calc R 1
C C8 -0.0976(4) 0.1414(2) 0.0708(4) 0.0542(10) Uani d . 1
H H8A -0.1447 0.0973 0.0620 0.065 Uiso calc R 1
C C9 -0.0482(4) 0.1743(2) 0.1943(4) 0.0510(10) Uani d . 1
H H9A -0.0580 0.1556 0.2785 0.061 Uiso calc R 1
C C10 0.3039(4) 0.31259(19) 0.0180(3) 0.0403(8) Uani d . 1
C C11 0.3328(4) 0.2446(2) -0.0182(4) 0.0498(9) Uani d . 1
H H11A 0.2584 0.2131 -0.0572 0.060 Uiso calc R 1
C C12 0.4781(5) 0.2225(2) 0.0045(4) 0.0574(11) Uani d . 1
H H12A 0.4982 0.1762 -0.0211 0.069 Uiso calc R 1
C C13 0.5882(5) 0.2673(2) 0.0627(4) 0.0603(11) Uani d . 1
H H13A 0.6825 0.2515 0.0761 0.072 Uiso calc R 1
C C14 0.5612(4) 0.3372(2) 0.1027(4) 0.0496(10) Uani d . 1
C C15 0.6714(4) 0.3854(3) 0.1646(4) 0.0677(13) Uani d . 1
H H15A 0.7665 0.3704 0.1814 0.081 Uiso calc R 1
C C16 0.6431(5) 0.4528(3) 0.2002(5) 0.0746(13) Uani d . 1
H H16A 0.7185 0.4836 0.2397 0.089 Uiso calc R 1
C C17 0.5021(5) 0.4765(2) 0.1781(4) 0.0655(12) Uani d . 1
H H17A 0.4837 0.5230 0.2040 0.079 Uiso calc R 1
C C18 0.3900(4) 0.4320(2) 0.1186(4) 0.0481(9) Uani d . 1
H H18A 0.2961 0.4485 0.1038 0.058 Uiso calc R 1
C C19 0.4161(4) 0.36147(19) 0.0798(3) 0.0409(8) 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C9 S C6 91.74(18) yes
C10 O C5 119.6(3) yes
C2 N C3 111.4(3) yes
C2 N C1 110.1(3) yes
C3 N C1 111.9(3) yes
N C1 H1A 109.5 ?
N C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
N C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
N C2 H2A 109.5 ?
N C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
N C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
N C3 C4 113.1(3) yes
N C3 H3A 109.0 ?
C4 C3 H3A 109.0 ?
N C3 H3B 109.0 ?
C4 C3 H3B 109.0 ?
H3A C3 H3B 107.8 ?
C5 C4 C3 112.7(3) ?
C5 C4 H4A 109.1 ?
C3 C4 H4A 109.1 ?
C5 C4 H4B 109.1 ?
C3 C4 H4B 109.1 ?
H4A C4 H4B 107.8 ?
O C5 C4 106.5(3) yes
O C5 C6 110.3(3) yes
C4 C5 C6 112.7(3) ?
O C5 H5A 109.1 ?
C4 C5 H5A 109.1 ?
C6 C5 H5A 109.1 ?
C7 C6 C5 127.5(3) ?
C7 C6 S 112.9(3) yes
C5 C6 S 119.4(3) yes
C6 C7 C8 108.0(3) ?
C6 C7 H7A 126.0 ?
C8 C7 H7A 126.0 ?
C9 C8 C7 114.8(3) ?
C9 C8 H8A 122.6 ?
C7 C8 H8A 122.6 ?
C8 C9 S 112.6(3) yes
C8 C9 H9A 123.7 ?
S C9 H9A 123.7 ?
C11 C10 O 125.2(3) yes
C11 C10 C19 121.4(3) ?
O C10 C19 113.3(3) yes
C10 C11 C12 119.1(4) ?
C10 C11 H11A 120.5 ?
C12 C11 H11A 120.5 ?
C13 C12 C11 121.4(4) ?
C13 C12 H12A 119.3 ?
C11 C12 H12A 119.3 ?
C12 C13 C14 120.6(4) ?
C12 C13 H13A 119.7 ?
C14 C13 H13A 119.7 ?
C13 C14 C15 122.7(4) ?
C13 C14 C19 119.4(4) ?
C15 C14 C19 117.8(4) ?
C16 C15 C14 121.8(4) ?
C16 C15 H15A 119.1 ?
C14 C15 H15A 119.1 ?
C15 C16 C17 120.5(4) ?
C15 C16 H16A 119.8 ?
C17 C16 H16A 119.8 ?
C18 C17 C16 120.5(4) ?
C18 C17 H17A 119.8 ?
C16 C17 H17A 119.8 ?
C17 C18 C19 120.4(4) ?
C17 C18 H18A 119.8 ?
C19 C18 H18A 119.8 ?
C18 C19 C10 122.9(3) ?
C18 C19 C14 119.0(3) ?
C10 C19 C14 118.1(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C6 1.709(3) yes
S C9 1.683(4) yes
O C10 1.370(4) yes
O C5 1.443(4) yes
N C2 1.440(5) yes
N C3 1.455(5) yes
N C1 1.462(5) yes
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 C4 1.517(5) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C5 1.511(5) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C6 1.513(5) ?
C5 H5A 0.9800 ?
C6 C7 1.410(5) ?
C7 C8 1.435(5) ?
C7 H7A 0.9300 ?
C8 C9 1.343(5) ?
C8 H8A 0.9300 ?
C9 H9A 0.9300 ?
C10 C11 1.360(5) ?
C10 C19 1.425(5) ?
C11 C12 1.419(5) ?
C11 H11A 0.9300 ?
C12 C13 1.357(6) ?
C12 H12A 0.9300 ?
C13 C14 1.400(5) ?
C13 H13A 0.9300 ?
C14 C15 1.406(6) ?
C14 C19 1.429(5) ?
C15 C16 1.345(6) ?
C15 H15A 0.9300 ?
C16 C17 1.390(6) ?
C16 H16A 0.9300 ?
C17 C18 1.369(5) ?
C17 H17A 0.9300 ?
C18 C19 1.405(5) ?
C18 H18A 0.9300 ?
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
C2 N C3 C4 161.7(4)
C1 N C3 C4 -74.6(4)
N C3 C4 C5 176.9(3)
C10 O C5 C4 -157.5(3)
C10 O C5 C6 80.0(4)
C3 C4 C5 O 53.6(4)
C3 C4 C5 C6 174.6(3)
O C5 C6 C7 -154.8(3)
C4 C5 C6 C7 86.3(4)
O C5 C6 S 30.0(4)
C4 C5 C6 S -88.8(3)
C9 S C6 C7 0.6(3)
C9 S C6 C5 176.4(3)
C5 C6 C7 C8 -176.3(3)
S C6 C7 C8 -0.8(4)
C6 C7 C8 C9 0.7(5)
C7 C8 C9 S -0.3(4)
C6 S C9 C8 -0.2(3)
C5 O C10 C11 -10.8(5)
C5 O C10 C19 169.4(3)
O C10 C11 C12 179.3(3)
C19 C10 C11 C12 -0.9(5)
C10 C11 C12 C13 0.7(6)
C11 C12 C13 C14 0.2(6)
C12 C13 C14 C15 179.4(4)
C12 C13 C14 C19 -1.0(6)
C13 C14 C15 C16 178.9(4)
C19 C14 C15 C16 -0.8(6)
C14 C15 C16 C17 0.9(7)
C15 C16 C17 C18 -0.7(7)
C16 C17 C18 C19 0.4(6)
C17 C18 C19 C10 179.7(3)
C17 C18 C19 C14 -0.3(5)
C11 C10 C19 C18 -179.9(3)
O C10 C19 C18 -0.1(5)
C11 C10 C19 C14 0.2(5)
O C10 C19 C14 180.0(3)
C13 C14 C19 C18 -179.2(3)
C15 C14 C19 C18 0.5(5)
C13 C14 C19 C10 0.8(5)
C15 C14 C19 C10 -179.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9747962
