#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/73/2017388.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_2017388
loop_
_publ_author_name
'Churakov, Andrei V.'
'Lermontova, Elmira Kh.'
'Zaitsev, Kirill V.'
'Huang, Mengmeng'
'Karlov, Sergey S.'
'Zaitseva, Galina S.'
'Howard, Judith A. K.'
_publ_section_title
;
 Crystal packing in the structures of diethanolamine derivatives
;
_journal_coeditor_code           GD3304
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o587
_journal_page_last               o592
_journal_paper_doi               10.1107/S0108270109036749
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H21 N O2'
_chemical_formula_moiety         'C17 H21 N O2'
_chemical_formula_sum            'C17 H21 N O2'
_chemical_formula_weight         271.35
_chemical_name_systematic
;
2-[(2-hydroxyethyl)(methyl)amino]-1,1-diphenylethanol
;
_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                 114.4410(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3438(2)
_cell_length_b                   15.9896(4)
_cell_length_c                   10.9479(3)
_cell_measurement_reflns_used    4201
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.982
_cell_measurement_theta_min      2.406
_cell_volume                     1489.08(6)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1K'
_diffrn_measurement_method       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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10283
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.184
_refine_ls_extinction_coef       0.0050(15)
_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   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0435
_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)+(0.0376P)²+0.2784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2508
_reflns_number_total             3416
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3304.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017388
_cod_database_fobs_code          2017388
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_disorder_assembly
_atom_site_disorder_group
N N1 0.85622(13) 0.05759(7) 0.74752(11) 0.0209(3) Uani d . 1 . .
O O1 1.00400(13) -0.06277(7) 0.64116(13) 0.0371(3) Uani d . 1 . .
O O2 0.80726(11) 0.09856(6) 0.49626(10) 0.0230(2) Uani d . 1 . .
C C1 1.09664(17) -0.00902(9) 0.74820(15) 0.0274(3) Uani d . 1 . .
H H1A 1.1236 0.0425 0.7121 0.033 Uiso calc R 1 . .
H H1B 1.1956 -0.0374 0.8066 0.033 Uiso calc R 1 . .
C C2 1.00289(17) 0.01278(9) 0.82778(14) 0.0263(3) Uani d . 1 . .
H H2A 0.9771 -0.0393 0.8633 0.032 Uiso calc R 1 . .
H H2B 1.0682 0.0480 0.9052 0.032 Uiso calc R 1 . .
C C3 0.74175(17) 0.05058(9) 0.80697(15) 0.0263(3) Uani d . 1 . .
H H3A 0.6438 0.0786 0.7489 0.039 Uiso calc R 1 . .
H H3B 0.7845 0.0771 0.8956 0.039 Uiso calc R 1 . .
H H3C 0.7206 -0.0086 0.8161 0.039 Uiso calc R 1 . .
C C4 0.88563(16) 0.14520(8) 0.72346(13) 0.0202(3) Uani d . 1 . .
H H4A 0.9992 0.1534 0.7478 0.024 Uiso calc R 1 . .
H H4B 0.8545 0.1826 0.7803 0.024 Uiso calc R 1 . .
C C5 0.78997(15) 0.16750(8) 0.57320(13) 0.0183(3) Uani d . 1 . .
C C6 0.61520(15) 0.18108(8) 0.54241(13) 0.0196(3) Uani d . 1 . .
C C7 0.56931(16) 0.25041(9) 0.59572(14) 0.0240(3) Uani d . 1 . .
H H7 0.6460 0.2898 0.6486 0.029 Uiso calc R 1 . .
C C8 0.41220(17) 0.26216(9) 0.57198(16) 0.0291(3) Uani d . 1 . .
H H8 0.3825 0.3094 0.6088 0.035 Uiso calc R 1 . .
C C9 0.29885(17) 0.20507(10) 0.49461(15) 0.0315(4) Uani d . 1 . .
H H9 0.1916 0.2133 0.4777 0.038 Uiso calc R 1 . .
C C10 0.34365(17) 0.13601(10) 0.44236(15) 0.0297(4) Uani d . 1 . .
H H10 0.2668 0.0965 0.3902 0.036 Uiso calc R 1 . .
C C11 0.50079(16) 0.12408(9) 0.46581(14) 0.0251(3) Uani d . 1 . .
H H11 0.5299 0.0766 0.4291 0.030 Uiso calc R 1 . .
C C12 0.85580(15) 0.24542(8) 0.53429(13) 0.0184(3) Uani d . 1 . .
C C13 0.93583(16) 0.30651(8) 0.62954(14) 0.0233(3) Uani d . 1 . .
H H13 0.9503 0.2994 0.7201 0.028 Uiso calc R 1 . .
C C14 0.99440(17) 0.37765(9) 0.59293(15) 0.0259(3) Uani d . 1 . .
H H14 1.0483 0.4188 0.6584 0.031 Uiso calc R 1 . .
C C15 0.97449(17) 0.38869(9) 0.46163(16) 0.0279(3) Uani d . 1 . .
H H15 1.0154 0.4371 0.4370 0.033 Uiso calc R 1 . .
C C16 0.89443(18) 0.32875(9) 0.36600(15) 0.0270(3) Uani d . 1 . .
H H16 0.8799 0.3364 0.2756 0.032 Uiso calc R 1 . .
C C17 0.83539(16) 0.25766(8) 0.40184(14) 0.0219(3) Uani d . 1 . .
H H17 0.7807 0.2170 0.3356 0.026 Uiso calc R 1 . .
H H1 1.060(2) -0.0751(12) 0.596(2) 0.062(6) Uiso d . 1 . .
H H2 0.816(2) 0.0551(12) 0.547(2) 0.053(6) Uiso 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'
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
C3 N1 C4 . . 112.09(11) no
C3 N1 C2 . . 111.55(11) no
C4 N1 C2 . . 111.92(11) no
C1 O1 H1 . . 107.3(14) no
C5 O2 H2 . . 104.0(13) no
O1 C1 C2 . . 108.32(12) no
O1 C1 H1A . . 110.0 no
C2 C1 H1A . . 110.0 no
O1 C1 H1B . . 110.0 no
C2 C1 H1B . . 110.0 no
H1A C1 H1B . . 108.4 no
N1 C2 C1 . . 112.77(11) no
N1 C2 H2A . . 109.0 no
C1 C2 H2A . . 109.0 no
N1 C2 H2B . . 109.0 no
C1 C2 H2B . . 109.0 no
H2A C2 H2B . . 107.8 no
N1 C3 H3A . . 109.5 no
N1 C3 H3B . . 109.5 no
H3A C3 H3B . . 109.5 no
N1 C3 H3C . . 109.5 no
H3A C3 H3C . . 109.5 no
H3B C3 H3C . . 109.5 no
N1 C4 C5 . . 109.85(10) no
N1 C4 H4A . . 109.7 no
C5 C4 H4A . . 109.7 no
N1 C4 H4B . . 109.7 no
C5 C4 H4B . . 109.7 no
H4A C4 H4B . . 108.2 no
O2 C5 C12 . . 107.87(10) no
O2 C5 C6 . . 110.25(10) no
C12 C5 C6 . . 109.70(10) no
O2 C5 C4 . . 106.84(10) no
C12 C5 C4 . . 111.16(10) no
C6 C5 C4 . . 110.94(10) no
C11 C6 C7 . . 118.59(13) no
C11 C6 C5 . . 121.36(12) no
C7 C6 C5 . . 120.01(12) no
C8 C7 C6 . . 120.64(13) no
C8 C7 H7 . . 119.7 no
C6 C7 H7 . . 119.7 no
C9 C8 C7 . . 120.23(14) no
C9 C8 H8 . . 119.9 no
C7 C8 H8 . . 119.9 no
C10 C9 C8 . . 119.41(14) no
C10 C9 H9 . . 120.3 no
C8 C9 H9 . . 120.3 no
C9 C10 C11 . . 120.51(14) no
C9 C10 H10 . . 119.7 no
C11 C10 H10 . . 119.7 no
C6 C11 C10 . . 120.61(14) no
C6 C11 H11 . . 119.7 no
C10 C11 H11 . . 119.7 no
C17 C12 C13 . . 118.55(12) no
C17 C12 C5 . . 120.45(12) no
C13 C12 C5 . . 121.00(12) no
C14 C13 C12 . . 120.59(13) no
C14 C13 H13 . . 119.7 no
C12 C13 H13 . . 119.7 no
C15 C14 C13 . . 120.29(14) no
C15 C14 H14 . . 119.9 no
C13 C14 H14 . . 119.9 no
C14 C15 C16 . . 119.65(13) no
C14 C15 H15 . . 120.2 no
C16 C15 H15 . . 120.2 no
C15 C16 C17 . . 120.34(13) no
C15 C16 H16 . . 119.8 no
C17 C16 H16 . . 119.8 no
C16 C17 C12 . . 120.57(13) no
C16 C17 H17 . . 119.7 no
C12 C17 H17 . . 119.7 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
N1 C3 . 1.4684(17) no
N1 C4 . 1.4722(16) no
N1 C2 . 1.4721(17) no
O1 C1 . 1.4219(18) no
O1 H1 . 0.88(2) no
O2 C5 . 1.4364(15) no
O2 H2 . 0.87(2) no
C1 C2 . 1.510(2) no
C1 H1A . 0.9900 no
C1 H1B . 0.9900 no
C2 H2A . 0.9900 no
C2 H2B . 0.9900 no
C3 H3A . 0.9800 no
C3 H3B . 0.9800 no
C3 H3C . 0.9800 no
C4 C5 . 1.5541(18) no
C4 H4A . 0.9900 no
C4 H4B . 0.9900 no
C5 C12 . 1.5261(18) no
C5 C6 . 1.5402(18) no
C6 C11 . 1.3909(19) no
C6 C7 . 1.4002(19) no
C7 C8 . 1.394(2) no
C7 H7 . 0.9500 no
C8 C9 . 1.389(2) no
C8 H8 . 0.9500 no
C9 C10 . 1.386(2) no
C9 H9 . 0.9500 no
C10 C11 . 1.395(2) no
C10 H10 . 0.9500 no
C11 H11 . 0.9500 no
C12 C17 . 1.3959(19) no
C12 C13 . 1.3984(19) no
C13 C14 . 1.3913(19) no
C13 H13 . 0.9500 no
C14 C15 . 1.382(2) no
C14 H14 . 0.9500 no
C15 C16 . 1.388(2) no
C15 H15 . 0.9500 no
C16 C17 . 1.3891(19) no
C16 H16 . 0.9500 no
C17 H17 . 0.9500 no
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
O2 H2 N1 . 0.87(2) 2.07(2) 2.6765(15) 126.0(16)
O1 H1 O2 3_756 0.88(2) 1.93(2) 2.8101(15) 177(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 98022
