#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/07/2010789.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_2010789
loop_
_publ_author_name
'Hempel, Andrew'
'Camerman, Norman'
'Dauter, Zbigniew'
'Mastropaolo, Donald'
'Camerman, Arthur'
_publ_section_title
;
 The antiestrogen [2-(4-benzylphenoxy)ethyl]diethylammonium chloride
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              455
_journal_page_last               456
_journal_paper_doi               10.1107/S0108270199016741
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C19 H26 N O+ , Cl-'
_chemical_formula_sum            'C19 H26 Cl N O'
_chemical_formula_weight         319.86
_chemical_name_common            DPPE
_chemical_name_systematic
;
[2-(4-benzylphenoxy)ethyl]diethylammonium chloride
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                   16.427(2)
_cell_length_b                   15.195(2)
_cell_length_c                   7.1940(10)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7
_cell_measurement_theta_min      2.4
_cell_volume                     1795.7(4)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'DENZO-SMN (Otwinowski & Minor,1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1998)'
_computing_publication_material  SHELX97
_computing_structure_refinement  SHELX97
_computing_structure_solution    SHELX97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .983
_diffrn_measured_fraction_theta_max .983
_diffrn_measurement_device_type  'ADSC Quantum-4 CCD detector'
_diffrn_measurement_method       'single axis rotation method'
_diffrn_radiation_monochromator  'double Si111 monochromator'
_diffrn_radiation_source         'X9B beamline at NSLS (Brookhaven)'
_diffrn_radiation_type           'synchrotron radiation'
_diffrn_radiation_wavelength     .92000(10)
_diffrn_reflns_av_R_equivalents  .051
_diffrn_reflns_av_sigmaI/netI    .042
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7875
_diffrn_reflns_theta_full        30.72
_diffrn_reflns_theta_max         30.72
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    .44
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          .130
_exptl_crystal_size_mid          .010
_exptl_crystal_size_min          .008
_refine_diff_density_max         .14
_refine_diff_density_min         -.19
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .58(5)
_refine_ls_extinction_coef       .0153(18)
_refine_ls_extinction_method     'SHELX97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          .041
_refine_ls_R_factor_gt           .036
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0618P)²+0.388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .105
_reflns_number_gt                2237
_reflns_number_total             2438
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bk1510.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1795.7(5)
_cod_database_code               2010789
_cod_database_fobs_code          2010789
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
loop_
_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
_atom_site_type_symbol
Cl1 .11651(4) .37167(5) -.11216(12) .0589(3) Uani d . 1 . . Cl
C1 .0698(3) 1.0333(4) -.3818(7) .0997(16) Uani d . 1 . . C
H1 .0439 1.0585 -.4836 .075(4) Uiso calc R 1 . . H
C2 .1128(3) 1.0843(3) -.2636(8) .0947(16) Uani d . 1 . . C
H2 .1162 1.1446 -.2842 .075(4) Uiso calc R 1 . . H
C3 .1514(2) 1.0481(2) -.1145(6) .0663(9) Uani d . 1 . . C
H3 .1807 1.0841 -.0343 .075(4) Uiso calc R 1 . . H
C4 .14756(16) .95850(18) -.0804(4) .0450(7) Uani d . 1 . . C
C5 .10378(18) .9069(2) -.2001(5) .0550(8) Uani d . 1 . . C
H5 .1005 .8466 -.1798 .075(4) Uiso calc R 1 . . H
C6 .0643(2) .9438(3) -.3514(5) .0785(12) Uani d . 1 . . C
H6 .0343 .9086 -.4318 .075(4) Uiso calc R 1 . . H
C7 .1935(2) .9229(2) .0859(5) .0609(9) Uani d . 1 . . C
H7A .2513 .9295 .0623 .063(3) Uiso calc R 1 . . H
H7B .1803 .9591 .1929 .063(3) Uiso calc R 1 . . H
C8 .17716(18) .82813(19) .1356(4) .0482(7) Uani d . 1 . . C
C9 .23448(18) .76344(19) .1009(4) .0479(8) Uani d . 1 . . C
H9 .2828 .7784 .0413 .075(4) Uiso calc R 1 . . H
C10 .22130(16) .67623(18) .1533(4) .0430(7) Uani d . 1 . . C
H10 .2603 .6335 .1286 .075(4) Uiso calc R 1 . . H
C11 .15009(16) .65414(18) .2418(4) .0405(6) Uani d . 1 . . C
C12 .09005(16) .71713(19) .2721(4) .0458(7) Uani d . 1 . . C
H12 .0409 .7016 .3273 .075(4) Uiso calc R 1 . . H
C13 .10439(18) .8027(2) .2193(4) .0495(7) Uani d . 1 . . C
H13 .0644 .8449 .2401 .075(4) Uiso calc R 1 . . H
O14 .13224(11) .57160(12) .3101(3) .0491(5) Uani d . 1 . . O
C15 .19018(15) .50310(16) .2790(4) .0421(7) Uani d . 1 . . C
H15A .2441 .5232 .3142 .063(3) Uiso calc R 1 . . H
H15B .1912 .4879 .1481 .063(3) Uiso calc R 1 . . H
C16 .16762(15) .42385(17) .3917(4) .0423(6) Uani d . 1 . . C
H16A .1558 .4426 .5177 .063(3) Uiso calc R 1 . . H
H16B .2141 .3846 .3968 .063(3) Uiso calc R 1 . . H
N17 .09552(14) .37339(14) .3183(3) .0395(5) Uani d . 1 . . N
H17 .0982 .3732 .1919 .063(3) Uiso calc R 1 . . H
C18 .09807(19) .28006(18) .3844(6) .0565(8) Uani d . 1 . . C
H18A .0465 .2520 .3564 .063(3) Uiso calc R 1 . . H
H18B .1050 .2796 .5183 .063(3) Uiso calc R 1 . . H
C19 .1658(3) .2277(2) .2967(7) .0833(12) Uani d . 1 . . C
H19A .1620(10) .2320(15) .164(3) .111(7) Uiso calc R 1 . . H
H19B .1612(11) .1674(16) .333(3) .111(7) Uiso calc R 1 . . H
H19C .2171(13) .2505(13) .337(3) .111(7) Uiso calc R 1 . . H
C20 .01646(14) .41786(19) .3756(5) .0459(7) Uani d . 1 . . C
H20A .0088 .4103 .5084 .063(3) Uiso calc R 1 . . H
H20B .0207 .4805 .3510 .063(3) Uiso calc R 1 . . H
C21 -.05657(19) .3821(2) .2758(5) .0628(9) Uani d . 1 . . C
H21A -.0466(7) .3841(17) .136(3) .111(7) Uiso calc R 1 . . H
H21B -.1064(13) .4193(14) .308(3) .111(7) Uiso calc R 1 . . H
H21C -.0664(10) .3186(16) .316(3) .111(7) Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .003 .003 'Cromer, D. T. (1983). J. Appl. Cryst. 16, 437-438'
H H .000 .000 'Cromer, D. T. (1983). J. Appl. Cryst. 16, 437-438'
N N .007 .006 'Cromer, D. T. (1983). J. Appl. Cryst. 16, 437-438'
O O .013 .011 'Cromer, D. T. (1983). J. Appl. Cryst. 16, 437-438'
Cl Cl .194 .265 'Cromer, D. T. (1983). J. Appl. Cryst. 16, 437-438'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 120.0(4)
C2 C1 H1 120.0
C6 C1 H1 120.0
C1 C2 C3 120.5(4)
C1 C2 H2 119.7
C3 C2 H2 119.7
C2 C3 C4 121.1(4)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 118.4(3)
C5 C4 C7 123.7(3)
C3 C4 C7 117.9(3)
C4 C5 C6 120.6(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 119.5(4)
C1 C6 H6 120.3
C5 C6 H6 120.3
C8 C7 C4 116.1(3)
C8 C7 H7A 108.3
C4 C7 H7A 108.3
C8 C7 H7B 108.3
C4 C7 H7B 108.3
H7A C7 H7B 107.4
C9 C8 C13 117.7(3)
C9 C8 C7 121.0(3)
C13 C8 C7 121.3(3)
C8 C9 C10 121.4(3)
C8 C9 H9 119.3
C10 C9 H9 119.3
C11 C10 C9 119.3(3)
C11 C10 H10 120.3
C9 C10 H10 120.3
O14 C11 C10 124.7(2)
O14 C11 C12 114.8(2)
C10 C11 C12 120.5(3)
C13 C12 C11 119.1(3)
C13 C12 H12 120.5
C11 C12 H12 120.5
C12 C13 C8 121.9(3)
C12 C13 H13 119.1
C8 C13 H13 119.1
C11 O14 C15 117.7(2)
O14 C15 C16 109.6(2)
O14 C15 H15A 109.7
C16 C15 H15A 109.7
O14 C15 H15B 109.7
C16 C15 H15B 109.7
H15A C15 H15B 108.2
C15 C16 N17 114.5(2)
C15 C16 H16A 108.6
N17 C16 H16A 108.6
C15 C16 H16B 108.6
N17 C16 H16B 108.6
H16A C16 H16B 107.6
C18 N17 C16 110.4(2)
C18 N17 C20 111.0(2)
C16 N17 C20 110.5(2)
C18 N17 H17 108.3
C16 N17 H17 108.3
C20 N17 H17 108.3
N17 C18 C19 112.8(3)
N17 C18 H18A 109.0
C19 C18 H18A 109.0
N17 C18 H18B 109.0
C19 C18 H18B 109.0
H18A C18 H18B 107.8
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C21 C20 N17 113.1(3)
C21 C20 H20A 109.0
N17 C20 H20A 109.0
C21 C20 H20B 109.0
N17 C20 H20B 109.0
H20A C20 H20B 107.8
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
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 C2 . 1.349(8) ?
C1 C6 . 1.381(7) ?
C1 H1 . .9300 ?
C2 C3 . 1.361(6) ?
C2 H2 . .9300 ?
C3 C4 . 1.384(4) ?
C3 H3 . .9300 ?
C4 C5 . 1.369(5) ?
C4 C7 . 1.514(4) ?
C5 C6 . 1.385(5) ?
C5 H5 . .9300 ?
C6 H6 . .9300 ?
C7 C8 . 1.508(4) ?
C7 H7A . .9700 ?
C7 H7B . .9700 ?
C8 C9 . 1.384(4) ?
C8 C13 . 1.393(4) ?
C9 C10 . 1.395(4) ?
C9 H9 . .9300 ?
C10 C11 . 1.373(4) ?
C10 H10 . .9300 ?
C11 O14 . 1.378(3) ?
C11 C12 . 1.392(4) ?
C12 C13 . 1.376(4) ?
C12 H12 . .9300 ?
C13 H13 . .9300 ?
O14 C15 . 1.428(3) ?
C15 C16 . 1.498(4) ?
C15 H15A . .9700 ?
C15 H15B . .9700 ?
C16 N17 . 1.506(3) ?
C16 H16A . .9700 ?
C16 H16B . .9700 ?
N17 C18 . 1.496(3) ?
N17 C20 . 1.521(3) ?
N17 H17 . .9100 ?
C18 C19 . 1.506(5) ?
C18 H18A . .9700 ?
C18 H18B . .9700 ?
C19 H19A . .9561 ?
C19 H19B . .9561 ?
C19 H19C . .9561 ?
C20 C21 . 1.500(4) ?
C20 H20A . .9700 ?
C20 H20B . .9700 ?
C21 H21A . 1.0207 ?
C21 H21B . 1.0207 ?
C21 H21C . 1.0207 ?
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
N17 H17 Cl1 1_555 .910(4) 2.208(4) 3.116(2) 174.9(2) n
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 .3(7)
C1 C2 C3 C4 .1(6)
C2 C3 C4 C5 -.2(5)
C2 C3 C4 C7 178.7(3)
C3 C4 C5 C6 -.1(5)
C7 C4 C5 C6 -178.9(3)
C2 C1 C6 C5 -.6(6)
C4 C5 C6 C1 .5(5)
C5 C4 C7 C8 -10.5(5)
C3 C4 C7 C8 170.7(3)
C4 C7 C8 C9 106.9(3)
C4 C7 C8 C13 -73.7(4)
C13 C8 C9 C10 -2.1(4)
C7 C8 C9 C10 177.3(3)
C8 C9 C10 C11 -.2(4)
C9 C10 C11 O14 -175.9(3)
C9 C10 C11 C12 2.7(4)
O14 C11 C12 C13 176.0(3)
C10 C11 C12 C13 -2.8(4)
C11 C12 C13 C8 .3(5)
C9 C8 C13 C12 2.1(4)
C7 C8 C13 C12 -177.4(3)
C10 C11 O14 C15 -3.1(4)
C12 C11 O14 C15 178.2(3)
C11 O14 C15 C16 169.7(2)
O14 C15 C16 N17 73.9(3)
C15 C16 N17 C18 156.5(2)
C15 C16 N17 C20 -80.3(3)
C16 N17 C18 C19 -69.7(4)
C20 N17 C18 C19 167.4(3)
C18 N17 C20 C21 -68.9(3)
C16 N17 C20 C21 168.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 152931
