#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/73/2017387.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_2017387
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          'C21 H27 N O2'
_chemical_formula_moiety         'C21 H27 N O2'
_chemical_formula_sum            'C21 H27 N O2'
_chemical_formula_weight         325.44
_chemical_name_systematic
;
1-{2-[hydroxy(diphenyl)methyl]pyrrolidin-1-yl}- 2-methylpropan-2-ol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5024(4)
_cell_length_b                   11.9480(5)
_cell_length_c                   17.6485(7)
_cell_measurement_reflns_used    6375
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.868
_cell_measurement_theta_min      2.308
_cell_volume                     1792.85(13)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12996
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0353
_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)+(0.0452P)²+0.2289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                2398
_reflns_number_total             2712
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3304.cif
_cod_data_source_block           II
_cod_database_code               2017387
_cod_database_fobs_code          2017387
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.35346(16) 0.52971(12) 0.27771(8) 0.0168(3) Uani d . 1 . .
O O1 0.28678(14) 0.74120(10) 0.30108(7) 0.0189(2) Uani d . 1 . .
O O2 0.66413(14) 0.47597(11) 0.20799(7) 0.0221(3) Uani d . 1 . .
C C1 0.5350(2) 0.52078(14) 0.16482(9) 0.0189(3) Uani d . 1 . .
C C2 0.37558(19) 0.48853(14) 0.19995(10) 0.0184(3) Uani d . 1 . .
C C3 0.5592(2) 0.64710(15) 0.16528(11) 0.0225(4) Uani d . 1 . .
C C4 0.5423(2) 0.47535(18) 0.08388(10) 0.0263(4) Uani d . 1 . .
C C5 0.4226(2) 0.45467(15) 0.33634(10) 0.0227(4) Uani d . 1 . .
C C6 0.2884(3) 0.42443(16) 0.38944(11) 0.0280(4) Uani d . 1 . .
C C7 0.1827(2) 0.52712(16) 0.38402(10) 0.0232(4) Uani d . 1 . .
C C8 0.18740(19) 0.55350(13) 0.29899(9) 0.0167(3) Uani d . 1 . .
C C9 0.14822(18) 0.67934(13) 0.28141(9) 0.0167(3) Uani d . 1 . .
C C10 0.10664(18) 0.70077(14) 0.19757(9) 0.0180(3) Uani d . 1 . .
C C11 0.1615(2) 0.79812(15) 0.16237(10) 0.0228(4) Uani d . 1 . .
C C12 0.1260(2) 0.82006(18) 0.08651(11) 0.0306(4) Uani d . 1 . .
C C13 0.0340(2) 0.7466(2) 0.04558(10) 0.0314(4) Uani d . 1 . .
C C14 -0.0230(2) 0.65083(18) 0.08018(10) 0.0279(4) Uani d . 1 . .
C C15 0.0126(2) 0.62770(16) 0.15586(10) 0.0224(4) Uani d . 1 . .
C C16 0.01362(19) 0.71839(13) 0.33306(9) 0.0172(3) Uani d . 1 . .
C C17 0.0390(2) 0.79870(15) 0.38896(10) 0.0218(3) Uani d . 1 . .
C C18 -0.0794(2) 0.82608(17) 0.44028(10) 0.0260(4) Uani d . 1 . .
C C19 -0.2242(2) 0.77320(16) 0.43673(10) 0.0247(4) Uani d . 1 . .
C C20 -0.2520(2) 0.69529(17) 0.37973(10) 0.0251(4) Uani d . 1 . .
C C21 -0.1349(2) 0.66812(15) 0.32815(10) 0.0226(4) Uani d . 1 . .
H H1 0.360(3) 0.695(2) 0.2932(14) 0.037(7) Uiso d . 1 . .
H H2 0.673(3) 0.406(2) 0.2018(15) 0.039(7) Uiso d . 1 . .
H H8 0.111(2) 0.5054(17) 0.2722(10) 0.016(5) Uiso d . 1 . .
H H11 0.226(3) 0.8489(19) 0.1884(13) 0.029(6) Uiso d . 1 . .
H H12 0.166(2) 0.8904(19) 0.0638(12) 0.024(5) Uiso d . 1 . .
H H13 0.004(3) 0.759(2) -0.0051(15) 0.040(6) Uiso d . 1 . .
H H14 -0.094(3) 0.5981(19) 0.0528(11) 0.026(5) Uiso d . 1 . .
H H15 -0.030(2) 0.5631(18) 0.1773(11) 0.021(5) Uiso d . 1 . .
H H17 0.141(2) 0.8358(17) 0.3923(11) 0.019(5) Uiso d . 1 . .
H H18 -0.063(3) 0.881(2) 0.4783(12) 0.030(6) Uiso d . 1 . .
H H19 -0.306(3) 0.7904(18) 0.4737(12) 0.026(5) Uiso d . 1 . .
H H20 -0.358(3) 0.6615(19) 0.3750(12) 0.027(6) Uiso d . 1 . .
H H21 -0.158(2) 0.6126(17) 0.2876(11) 0.015(5) Uiso d . 1 . .
H H22 0.294(2) 0.5219(18) 0.1672(11) 0.023(5) Uiso d . 1 . .
H H23 0.368(2) 0.4065(18) 0.1989(12) 0.022(5) Uiso d . 1 . .
H H31 0.650(3) 0.6659(19) 0.1338(12) 0.027(6) Uiso d . 1 . .
H H32 0.467(3) 0.6827(18) 0.1449(12) 0.024(5) Uiso d . 1 . .
H H33 0.573(2) 0.6771(18) 0.2192(12) 0.023(5) Uiso d . 1 . .
H H41 0.535(3) 0.393(2) 0.0857(12) 0.031(6) Uiso d . 1 . .
H H42 0.451(3) 0.507(2) 0.0521(13) 0.040(7) Uiso d . 1 . .
H H43 0.642(3) 0.4923(19) 0.0583(13) 0.028(6) Uiso d . 1 . .
H H51 0.506(3) 0.494(2) 0.3651(12) 0.032(6) Uiso d . 1 . .
H H52 0.473(3) 0.3898(19) 0.3115(12) 0.027(5) Uiso d . 1 . .
H H61 0.327(3) 0.409(2) 0.4391(14) 0.033(6) Uiso d . 1 . .
H H62 0.231(3) 0.358(2) 0.3697(12) 0.027(6) Uiso d . 1 . .
H H71 0.077(3) 0.513(2) 0.4013(13) 0.034(6) Uiso d . 1 . .
H H72 0.229(3) 0.589(2) 0.4111(13) 0.033(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
C2 N1 C8 . . 114.89(13) no
C2 N1 C5 . . 113.36(14) no
C8 N1 C5 . . 108.29(13) no
C9 O1 H1 . . 103.1(17) no
C1 O2 H2 . . 111.3(17) no
O2 C1 C3 . . 105.26(14) no
O2 C1 C4 . . 109.37(14) no
C3 C1 C4 . . 110.56(15) no
O2 C1 C2 . . 111.43(13) no
C3 C1 C2 . . 111.37(14) no
C4 C1 C2 . . 108.83(14) no
N1 C2 C1 . . 113.88(14) no
N1 C2 H22 . . 108.9(12) no
C1 C2 H22 . . 106.2(12) no
N1 C2 H23 . . 110.0(13) no
C1 C2 H23 . . 107.6(12) no
H22 C2 H23 . . 110.1(17) no
C1 C3 H31 . . 109.3(14) no
C1 C3 H32 . . 109.1(13) no
H31 C3 H32 . . 109.1(16) no
C1 C3 H33 . . 111.6(12) no
H31 C3 H33 . . 110.9(17) no
H32 C3 H33 . . 106.7(17) no
C1 C4 H41 . . 108.7(13) no
C1 C4 H42 . . 110.4(14) no
H41 C4 H42 . . 109.9(19) no
C1 C4 H43 . . 113.0(13) no
H41 C4 H43 . . 105.7(19) no
H42 C4 H43 . . 109.0(17) no
N1 C5 C6 . . 105.97(14) no
N1 C5 H51 . . 110.9(13) no
C6 C5 H51 . . 109.6(12) no
N1 C5 H52 . . 109.5(12) no
C6 C5 H52 . . 114.4(13) no
H51 C5 H52 . . 106.5(18) no
C5 C6 C7 . . 102.29(14) no
C5 C6 H61 . . 110.6(14) no
C7 C6 H61 . . 114.9(15) no
C5 C6 H62 . . 109.9(13) no
C7 C6 H62 . . 109.4(13) no
H61 C6 H62 . . 109(2) no
C6 C7 C8 . . 102.19(14) no
C6 C7 H71 . . 113.1(15) no
C8 C7 H71 . . 111.7(14) no
C6 C7 H72 . . 110.1(14) no
C8 C7 H72 . . 108.6(14) no
H71 C7 H72 . . 111(2) no
N1 C8 C7 . . 103.45(13) no
N1 C8 C9 . . 109.52(13) no
C7 C8 C9 . . 112.60(14) no
N1 C8 H8 . . 113.0(11) no
C7 C8 H8 . . 109.4(11) no
C9 C8 H8 . . 108.8(11) no
O1 C9 C16 . . 108.19(13) no
O1 C9 C10 . . 109.57(13) no
C16 C9 C10 . . 110.37(13) no
O1 C9 C8 . . 105.75(12) no
C16 C9 C8 . . 109.37(13) no
C10 C9 C8 . . 113.38(13) no
C15 C10 C11 . . 118.52(16) no
C15 C10 C9 . . 122.28(15) no
C11 C10 C9 . . 119.18(15) no
C12 C11 C10 . . 120.63(18) no
C12 C11 H11 . . 118.3(14) no
C10 C11 H11 . . 121.0(14) no
C13 C12 C11 . . 120.32(19) no
C13 C12 H12 . . 121.3(12) no
C11 C12 H12 . . 118.3(13) no
C12 C13 C14 . . 119.54(17) no
C12 C13 H13 . . 123.6(17) no
C14 C13 H13 . . 116.8(17) no
C13 C14 C15 . . 120.62(19) no
C13 C14 H14 . . 121.3(12) no
C15 C14 H14 . . 118.0(12) no
C10 C15 C14 . . 120.35(18) no
C10 C15 H15 . . 121.9(12) no
C14 C15 H15 . . 117.7(12) no
C17 C16 C21 . . 118.60(16) no
C17 C16 C9 . . 120.95(15) no
C21 C16 C9 . . 120.32(14) no
C18 C17 C16 . . 120.70(17) no
C18 C17 H17 . . 119.8(12) no
C16 C17 H17 . . 119.5(12) no
C19 C18 C17 . . 120.38(17) no
C19 C18 H18 . . 118.8(14) no
C17 C18 H18 . . 120.9(14) no
C18 C19 C20 . . 119.25(17) no
C18 C19 H19 . . 120.5(13) no
C20 C19 H19 . . 120.3(13) no
C21 C20 C19 . . 120.63(17) no
C21 C20 H20 . . 120.0(13) no
C19 C20 H20 . . 119.3(13) no
C20 C21 C16 . . 120.39(16) no
C20 C21 H21 . . 119.3(11) no
C16 C21 H21 . . 120.4(11) 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 C2 . 1.470(2) no
N1 C8 . 1.488(2) no
N1 C5 . 1.490(2) no
O1 C9 . 1.4334(19) no
O1 H1 . 0.84(3) no
O2 C1 . 1.439(2) no
O2 H2 . 0.85(3) no
C1 C3 . 1.523(2) no
C1 C4 . 1.530(2) no
C1 C2 . 1.540(2) no
C2 H22 . 0.98(2) no
C2 H23 . 0.98(2) no
C3 H31 . 0.98(2) no
C3 H32 . 0.96(2) no
C3 H33 . 1.02(2) no
C4 H41 . 0.99(2) no
C4 H42 . 1.03(3) no
C4 H43 . 0.99(2) no
C5 C6 . 1.520(3) no
C5 H51 . 0.99(2) no
C5 H52 . 0.99(2) no
C6 C7 . 1.524(3) no
C6 H61 . 0.96(2) no
C6 H62 . 0.99(2) no
C7 C8 . 1.534(2) no
C7 H71 . 0.96(3) no
C7 H72 . 0.96(2) no
C8 C9 . 1.571(2) no
C8 H8 . 0.99(2) no
C9 C16 . 1.536(2) no
C9 C10 . 1.543(2) no
C10 C15 . 1.394(2) no
C10 C11 . 1.399(2) no
C11 C12 . 1.397(3) no
C11 H11 . 0.94(2) no
C12 C13 . 1.380(3) no
C12 H12 . 0.99(2) no
C13 C14 . 1.385(3) no
C13 H13 . 0.94(3) no
C14 C15 . 1.397(3) no
C14 H14 . 1.00(2) no
C15 H15 . 0.93(2) no
C16 C17 . 1.393(2) no
C16 C21 . 1.401(2) no
C17 C18 . 1.393(3) no
C17 H17 . 0.98(2) no
C18 C19 . 1.386(3) no
C18 H18 . 0.95(2) no
C19 C20 . 1.391(3) no
C19 H19 . 0.98(2) no
C20 C21 . 1.388(2) no
C20 H20 . 0.99(2) no
C21 H21 . 0.99(2) 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
O1 H1 N1 . 0.84(3) 1.99(3) 2.6223(18) 131(2)
O2 H2 O1 3_645 0.85(3) 1.99(3) 2.8404(17) 172(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25936541
