#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008196.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_2008196
loop_
_publ_author_name
'Khoo, L. E.'
'Hu, H. J.'
'Hazell, A.'
_publ_section_title
;
 4-Chloro-2-[2-(dimethylamino)ethylaminomethyl]phenol and
 2-[2-(dimethylamino)ethylaminomethyl]-6-methoxyphenol
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              245
_journal_page_last               248
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C11 H17 Cl N2 O'
_chemical_formula_weight         228.73
_chemical_melting_point          336.5(15)
_chemical_name_systematic
;
2-[2-(dimethylamino)ethylaminomethyl]-4-chlorophenol
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   21.9350(10)
_cell_length_b                   11.4354(7)
_cell_length_c                   9.9743(6)
_cell_measurement_reflns_used    5045
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.8
_cell_measurement_theta_min      2.9
_cell_volume                     2501.9(2)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
      ORTEPIII (Burnett & Johnson, 1996) and  KRYSTAL
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement
'modified ORFLS (Busing et al., 1962) and KRYSTAL'
_computing_structure_solution
'SIR92 (Altomare et al., 1994) and  KRYSTAL (Hazell, 1995)'
_diffrn_ambient_temperature      295
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method
;
\w rotation scans with narrow frames
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14436
_diffrn_reflns_reduction_process 14436
_diffrn_reflns_theta_max         26.8
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   'multi-scan (SADABS; Siemens, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.23(4)
_refine_diff_density_min         -0.23(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1499
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.041
_refine_ls_shift/esd_max         0.0033
_refine_ls_shift/esd_mean        0.0004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
;
   1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^-|F|}^2^
;
_refine_ls_wR_factor_obs         0.046
_reflns_number_observed          1499
_reflns_number_total             2569
_reflns_observed_criterion       I>2\s(I)
_[local]_cod_data_source_file    sk1230.cif
_[local]_cod_data_source_block   1a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '335-338K' was changed to '336.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2008196
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,1/2-y,1/2+z
1/2+x,1/2-y,-z
-x,+y,1/2-z
-x,-y,-z
1/2+x,1/2+y,1/2-z
1/2-x,1/2+y,+z
+x,-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.1080(6) 0.0416(4) 0.0664(5) -0.0031(4) 0.0002(4) -0.0112(3)
O1 0.0920(10) 0.0390(10) 0.0420(10) 0.0120(10) 0.0140(10) 0.0100(10)
C1 0.0470(10) 0.0400(10) 0.0360(10) 0.0060(10) 0.0040(10) 0.0020(10)
C2 0.066(2) 0.052(2) 0.0310(10) 0.0060(10) 0.0050(10) 0.0040(10)
C3 0.064(2) 0.056(2) 0.0340(10) 0.0040(10) 0.0020(10) -0.0100(10)
C4 0.052(2) 0.0400(10) 0.0430(10) -0.0010(10) -0.0010(10) -0.0070(10)
C5 0.0470(10) 0.0420(10) 0.0370(10) -0.0010(10) 0.0000(10) 0.0040(10)
C6 0.0400(10) 0.0410(10) 0.0310(10) 0.0030(10) 0.0030(10) 0.0000(10)
C7 0.058(2) 0.0430(10) 0.0370(10) 0.0040(10) 0.0120(10) 0.0000(10)
N1 0.073(2) 0.0370(10) 0.0360(10) 0.0020(10) 0.0070(10) -0.0010(10)
C8 0.083(2) 0.049(2) 0.049(2) 0.0000(10) -0.0070(10) 0.0050(10)
C9 0.085(2) 0.061(2) 0.064(2) -0.006(2) -0.020(2) -0.0030(10)
N2 0.072(2) 0.0510(10) 0.070(2) -0.0090(10) -0.0100(10) 0.0060(10)
C10 0.099(3) 0.084(2) 0.081(2) 0.005(2) 0.006(2) 0.007(2)
C11 0.094(3) 0.076(2) 0.133(3) -0.023(2) -0.017(2) 0.014(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Cl 0.92040(4) 0.55243(5) 1.16671(7) 0.0720(5) Uij
O1 0.92920(10) 0.04020(10) 1.1492(2) 0.0580(10) Uij
C1 0.92690(10) 0.1580(2) 1.1587(2) 0.0410(10) Uij
C2 0.91510(10) 0.2168(2) 1.2776(2) 0.050(2) Uij
C3 0.91330(10) 0.3374(2) 1.2806(2) 0.051(2) Uij
C4 0.92330(10) 0.3994(2) 1.1647(2) 0.0450(10) Uij
C5 0.93560(10) 0.3424(2) 1.0459(2) 0.0420(10) Uij
C6 0.93810(10) 0.2214(2) 1.0413(2) 0.0370(10) Uij
C7 0.95150(10) 0.1563(2) 0.9135(2) 0.0460(10) Uij
N1 0.89950(10) 0.0892(2) 0.8605(2) 0.0490(10) Uij
C8 0.85010(10) 0.1637(2) 0.8096(2) 0.060(2) Uij
C9 0.79150(10) 0.0951(2) 0.8021(3) 0.070(2) Uij
N2 0.77240(10) 0.0515(2) 0.9324(3) 0.064(2) Uij
C10 0.74970(10) 0.1441(3) 1.0171(3) 0.088(2) Uij
C11 0.7269(2) -0.0402(3) 0.9182(4) 0.101(3) Uij
HN1 0.8850(10) 0.053(2) 0.923(2) 0.044(8) Uiso
HO1 0.9190(10) 0.006(3) 1.228(3) 0.083(10) Uiso
H2 0.9083 0.1737 1.3576 0.060 Uiso
H3 0.9053 0.3772 1.3623 0.061 Uiso
H5 0.9425 0.3865 0.9666 0.050 Uiso
H7a 0.9636 0.2115 0.8475 0.056 Uiso
H7b 0.9840 0.1035 0.9302 0.056 Uiso
H8a 0.8448 0.2285 0.8680 0.072 Uiso
H8b 0.8605 0.1911 0.7226 0.072 Uiso
H9a 0.7604 0.1445 0.7676 0.084 Uiso
H9b 0.7972 0.0306 0.7435 0.084 Uiso
H10a 0.7372 0.1155 1.1023 0.106 Uiso
H10b 0.7810 0.2004 1.0295 0.106 Uiso
H10c 0.7157 0.1798 0.9744 0.106 Uiso
H11a 0.7144 -0.0687 1.0034 0.122 Uiso
H11b 0.6924 -0.0095 0.8725 0.122 Uiso
H11c 0.7437 -0.1028 0.8677 0.122 Uiso
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . 123.4(2) yes
O1 C1 C6 . 116.8(2) yes
C2 C1 C6 . 119.8(2) no
C1 C2 C3 . 120.5(2) no
C2 C3 C4 . 119.6(2) no
C3 C4 C5 . 120.7(2) no
Cl C4 C3 . 120.0(2) yes
Cl C4 C5 . 119.3(2) yes
C4 C5 C6 . 120.5(2) no
C1 C6 C5 . 118.9(2) no
C5 C6 C7 . 122.0(2) no
C1 C6 C7 . 119.1(2) yes
C6 C7 N1 . 114.2(2) yes
C7 N1 C8 . 113.1(2) yes
N1 C8 C9 . 110.1(2) yes
C8 C9 N2 . 112.3(2) no
C9 N2 C10 . 111.8(2) no
C10 N2 C11 . 110.3(3) no
C9 N2 C11 . 111.0(3) no
C1 O1 HO1 . 111(2) no
C3 C2 H2 . 119.7 no
C1 C2 H2 . 119.7 no
C4 C3 H3 . 120.2 no
C2 C3 H3 . 120.2 no
C4 C5 H5 . 119.7 no
C6 C5 H5 . 119.7 no
H7a C7 H7b . 109.5 no
N1 C7 H7a . 108.3 no
C6 C7 H7a . 108.3 no
N1 C7 H7b . 108.3 no
C6 C7 H7b . 108.3 no
C8 N1 HN1 . 106(2) no
C7 N1 HN1 . 107(2) no
HN1 N1 HO1 8_554 111(2) no
C8 N1 HO1 8_554 106.3 no
C7 N1 HO1 8_554 113.6 no
H8a C8 H8b . 109.5 no
N1 C8 H8a . 109.3 no
C9 C8 H8a . 109.3 no
N1 C8 H8b . 109.3 no
C9 C8 H8b . 109.3 no
H9a C9 H9b . 109.5 no
N2 C9 H9a . 108.8 no
C8 C9 H9a . 108.8 no
N2 C9 H9b . 108.8 no
C8 C9 H9b . 108.8 no
H10a C10 H10b . 108.9 no
H10a C10 H10c . 108.9 no
N2 C10 H10a . 111.8 no
H10b C10 H10c . 109.5 no
N2 C10 H10b . 108.9 no
N2 C10 H10c . 108.9 no
H11a C11 H11b . 109.1 no
H11a C11 H11c . 109.1 no
N2 C11 H11a . 111.0 no
H11b C11 H11c . 109.5 no
N2 C11 H11b . 109.1 no
N2 C11 H11c . 109.1 no
O1 HO1 N1 8_555 167(3) no
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
Cl C4 . 1.751(2) yes
O1 C1 . 1.352(3) yes
C1 C2 . 1.387(3) no
C1 C6 . 1.399(3) no
C2 C3 . 1.379(3) no
C3 C4 . 1.374(3) no
C4 C5 . 1.379(3) no
C5 C6 . 1.385(3) no
C6 C7 . 1.505(3) yes
C7 N1 . 1.472(3) yes
N1 C8 . 1.469(3) yes
C8 C9 . 1.509(4) no
C9 N2 . 1.454(4) no
N2 C10 . 1.443(4) no
N2 C11 . 1.456(4) no
O1 HO1 . 0.90(3) no
C2 H2 . 0.950 no
C3 H3 . 0.950 no
C5 H5 . 0.950 no
C7 H7a . 0.950 no
C7 H7b . 0.950 no
N1 HN1 . 0.81(2) no
N1 HO1 8_554 1.77(3) no
C8 H8a . 0.950 no
C8 H8b . 0.950 no
C9 H9a . 0.950 no
C9 H9b . 0.950 no
C10 H10a . 0.950 no
C10 H10b . 0.950 no
C10 H10c . 0.950 no
C11 H11a . 0.950 no
C11 H11b . 0.950 no
C11 H11c . 0.950 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
O1 N1 3.005(3) no
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
_geom_torsion_publ_flag
C1 C6 C7 N1 67.5(3) no