#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/63/2236362.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_2236362
loop_
_publ_author_name
'Frey, Wolfgang'
'Ibrahim, Mohammad M.'
'Ali, Basem F.'
'Jäger, Volker'
_publ_section_title
;
 3-Methylamino-3-phenylpropan-1-ol
;
_journal_coeditor_code           IM2389
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2857
_journal_paper_doi               10.1107/S160053681203694X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H15 N O'
_chemical_formula_moiety         'C10 H15 N O'
_chemical_formula_sum            'C10 H15 N O'
_chemical_formula_weight         165.23
_chemical_name_systematic
;
3-Methylamino-3-phenylpropan-1-ol
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.119(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9816(8)
_cell_length_b                   23.8962(19)
_cell_length_c                   7.4653(8)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      21.0
_cell_volume                     995.40(19)
_computing_cell_refinement       'XSCANS (Bruker, 1996)'
_computing_data_collection       'XSCANS (Bruker, 1996)'
_computing_data_reduction        'XSCANS (Bruker, 1996)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_sigmaI/netI    0.0905
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3535
_diffrn_reflns_theta_full        67.46
_diffrn_reflns_theta_max         67.46
_diffrn_reflns_theta_min         3.70
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.223
_refine_ls_extinction_coef       0.026(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   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0714
_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)+(0.0232P)²+0.9564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                896
_reflns_number_total             1704
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2389.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2236362
_cod_database_fobs_code          2236362
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
_atom_site_symmetry_multiplicity
O O1 0.6223(4) 0.02730(9) 0.2754(3) 0.0633(7) Uani d . 1 1
H H1A 0.622(7) -0.0130(18) 0.351(6) 0.111(14) Uiso d . 1 1
N N1 1.3595(5) 0.07300(10) 0.5221(4) 0.0610(8) Uani d . 1 1
H H1B 1.458(6) 0.0688(12) 0.436(5) 0.063(9) Uiso d . 1 1
C C1 0.7636(6) 0.02462(14) 0.1583(5) 0.0639(9) Uani d . 1 1
H H1C 0.7208 0.0555 0.0681 0.077 Uiso calc R 1 1
H H1D 0.7277 -0.0099 0.0849 0.077 Uiso calc R 1 1
C C2 1.0300(5) 0.02701(12) 0.2739(4) 0.0564(8) Uani d . 1 1
H H2A 1.1168 0.0238 0.1868 0.068 Uiso calc R 1 1
H H2B 1.0732 -0.0049 0.3599 0.068 Uiso calc R 1 1
C C3 1.1102(5) 0.08083(12) 0.3929(4) 0.0565(8) Uani d . 1 1
H H3 1.0121 0.0848 0.4727 0.068 Uiso calc R 1 1
C C4 1.4610(8) 0.11951(15) 0.6516(6) 0.0922(14) Uani d . 1 1
H H4A 1.4654 0.1522 0.5782 0.138 Uiso calc R 1 1
H H4B 1.6207 0.1102 0.7351 0.138 Uiso calc R 1 1
H H4C 1.3637 0.1268 0.7270 0.138 Uiso calc R 1 1
C C5 1.0643(6) 0.13176(12) 0.2623(5) 0.0603(9) Uani d . 1 1
C C6 0.8826(7) 0.16881(14) 0.2513(6) 0.0790(11) Uani d . 1 1
H H6 0.7948 0.1640 0.3307 0.095 Uiso calc R 1 1
C C7 0.8291(8) 0.21376(16) 0.1211(7) 0.0936(14) Uani d . 1 1
H H7 0.7072 0.2387 0.1152 0.112 Uiso calc R 1 1
C C8 0.9553(9) 0.22067(16) 0.0047(7) 0.0925(14) Uani d . 1 1
H H8 0.9167 0.2496 -0.0844 0.111 Uiso calc R 1 1
C C9 1.1390(8) 0.18531(15) 0.0176(6) 0.0851(12) Uani d . 1 1
H H9 1.2292 0.1911 -0.0595 0.102 Uiso calc R 1 1
C C10 1.1927(7) 0.14055(14) 0.1451(5) 0.0737(10) Uani d . 1 1
H H10 1.3169 0.1163 0.1511 0.088 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 H1A 112(2)
C4 N1 C3 114.9(3)
C4 N1 H1B 107.1(17)
C3 N1 H1B 106.3(18)
O1 C1 C2 112.6(3)
O1 C1 H1C 109.1
C2 C1 H1C 109.1
O1 C1 H1D 109.1
C2 C1 H1D 109.1
H1C C1 H1D 107.8
C1 C2 C3 113.9(3)
C1 C2 H2A 108.8
C3 C2 H2A 108.8
C1 C2 H2B 108.8
C3 C2 H2B 108.8
H2A C2 H2B 107.7
N1 C3 C5 115.4(2)
N1 C3 C2 107.7(2)
C5 C3 C2 110.6(2)
N1 C3 H3 107.6
C5 C3 H3 107.6
C2 C3 H3 107.6
N1 C4 H4A 109.5
N1 C4 H4B 109.5
H4A C4 H4B 109.5
N1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C10 C5 C6 118.2(3)
C10 C5 C3 121.2(3)
C6 C5 C3 120.5(3)
C5 C6 C7 120.6(4)
C5 C6 H6 119.7
C7 C6 H6 119.7
C8 C7 C6 119.8(4)
C8 C7 H7 120.1
C6 C7 H7 120.1
C7 C8 C9 120.2(4)
C7 C8 H8 119.9
C9 C8 H8 119.9
C8 C9 C10 120.5(4)
C8 C9 H9 119.8
C10 C9 H9 119.8
C5 C10 C9 120.7(4)
C5 C10 H10 119.7
C9 C10 H10 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.420(4)
O1 H1A 1.12(4)
N1 C4 1.454(4)
N1 C3 1.468(4)
N1 H1B 1.02(4)
C1 C2 1.516(4)
C1 H1C 0.9700
C1 H1D 0.9700
C2 C3 1.538(4)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C5 1.521(4)
C3 H3 0.9800
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 C10 1.373(5)
C5 C6 1.381(4)
C6 C7 1.406(5)
C6 H6 0.9300
C7 C8 1.351(6)
C7 H7 0.9300
C8 C9 1.362(6)
C8 H8 0.9300
C9 C10 1.390(5)
C9 H9 0.9300
C10 H10 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
N1 H1B O1 1_655 1.02(4) 2.06(3) 3.023(4) 157(2)
O1 H1A N1 3_756 1.12(4) 1.70(4) 2.815(3) 176(3)
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
O1 C1 C2 C3 -60.3(4)
C4 N1 C3 C5 58.3(4)
C4 N1 C3 C2 -177.6(3)
C1 C2 C3 N1 169.9(3)
C1 C2 C3 C5 -63.0(3)
N1 C3 C5 C10 54.1(4)
C2 C3 C5 C10 -68.5(4)
N1 C3 C5 C6 -129.5(3)
C2 C3 C5 C6 107.9(3)
C10 C5 C6 C7 0.9(5)
C3 C5 C6 C7 -175.6(3)
C5 C6 C7 C8 0.4(6)
C6 C7 C8 C9 -2.1(7)
C7 C8 C9 C10 2.5(7)
C6 C5 C10 C9 -0.6(5)
C3 C5 C10 C9 175.9(3)
C8 C9 C10 C5 -1.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16137138
