#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229317.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_2229317
loop_
_publ_author_name
'Chakka, Sai Kumar'
'McKay, Michael G.'
'Govender, Thavendran'
'Kruger, Hendrik G.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 [(1R,3S)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol
 2.33-hydrate
;
_journal_coeditor_code           BG2388
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o700
_journal_paper_doi               10.1107/S1600536811006052
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H21 N1 O3, 2.33H2 O1'
_chemical_formula_moiety         'C18 H21 N1 O3, 2.33(H2 O1)'
_chemical_formula_sum            'C18 H25.67 N O5.33'
_chemical_formula_weight         341.39
_chemical_name_systematic
;
[(1R,3S)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-
3-yl]methanol 2.33-hydrate
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   27.950(2)
_cell_length_b                   27.950(2)
_cell_length_c                   5.8035(5)
_cell_measurement_reflns_used    10224
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.52
_cell_volume                     3926.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa DUO APEXII CCD'
_diffrn_measurement_method       '0.5° φ scans and 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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10224
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1650
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.304
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0561
_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)+(0.0985P)²+2.1271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                3707
_reflns_number_total             4340
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2388.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-03-21
;
_cod_original_cell_volume        3926(2)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               2229317
_cod_database_fobs_code          2229317
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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
_atom_site_attached_hydrogens
O O1 0.91196(8) 0.15356(9) 0.2897(4) 0.0468(5) Uani d . 1 . . 0
O O2 0.95248(8) 0.22297(9) 0.6202(3) 0.0484(5) Uani d . 1 . . 0
O O3 0.67745(12) 0.27007(15) 0.4378(6) 0.0809(9) Uani d D 1 . . 0
H H3O 0.675(2) 0.287(2) 0.291(5) 0.097 Uiso d D 1 . . 0
O O1W 0.6667 0.3333 0.0620(11) 0.0959(17) Uiso d S 1 . . 2
O O2W 0.82161(9) 0.36012(8) 0.0053(3) 0.0477(5) Uani d . 1 . . 2
O O3W 0.76609(13) 0.41438(12) -0.0962(6) 0.0806(8) Uani d . 1 . . 2
N N1 0.75539(10) 0.24710(8) 0.1792(4) 0.0370(5) Uani d D 1 . . 0
H H1N 0.7216(8) 0.2411(13) 0.108(5) 0.043 Uiso d D 1 . . 0
C C1 0.76741(9) 0.20211(9) 0.1292(4) 0.0285(4) Uani d . 1 . . 0
H H1 0.7785 0.2059 -0.0366 0.034 Uiso calc R 1 . . 0
C C2 0.81654(9) 0.20906(9) 0.2690(4) 0.0299(4) Uani d . 1 . . 0
C C3 0.84111(9) 0.17779(10) 0.2090(4) 0.0327(5) Uani d . 1 . . 0
H H3 0.8270 0.1529 0.0825 0.039 Uiso calc R 1 . . 0
C C4 0.88544(10) 0.18267(10) 0.3311(4) 0.0348(5) Uani d . 1 . . 0
C C5 0.90748(11) 0.22030(11) 0.5167(4) 0.0369(5) Uani d . 1 . . 0
C C6 0.88280(12) 0.25024(10) 0.5776(4) 0.0375(5) Uani d . 1 . . 0
H H6 0.8969 0.2749 0.7045 0.045 Uiso calc R 1 . . 0
C C7 0.83662(10) 0.24501(9) 0.4548(4) 0.0314(5) Uani d . 1 . . 0
C C8 0.81126(12) 0.27861(10) 0.5265(4) 0.0399(6) Uani d . 1 . . 0
H H8A 0.8346 0.3171 0.4722 0.048 Uiso calc R 1 . . 0
H H8B 0.8096 0.2793 0.6968 0.048 Uiso calc R 1 . . 0
C C9 0.75403(13) 0.25544(11) 0.4300(4) 0.0411(6) Uani d . 1 . . 0
H H9 0.7287 0.2193 0.5058 0.049 Uiso calc R 1 . . 0
C C10 0.73288(16) 0.29565(15) 0.4714(7) 0.0594(8) Uani d . 1 . . 0
H H10A 0.7417 0.3100 0.6310 0.071 Uiso calc R 1 . . 0
H H10B 0.7516 0.3274 0.3646 0.071 Uiso calc R 1 . . 0
C C11 0.71644(9) 0.14513(9) 0.1564(4) 0.0280(4) Uani d . 1 . . 0
C C12 0.70780(10) 0.11199(10) 0.3506(4) 0.0337(5) Uani d . 1 . . 0
H H12 0.7343 0.1252 0.4715 0.040 Uiso calc R 1 . . 0
C C13 0.66148(12) 0.06060(11) 0.3683(5) 0.0433(6) Uani d . 1 . . 0
H H13 0.6562 0.0387 0.5013 0.052 Uiso calc R 1 . . 0
C C14 0.62243(11) 0.04056(11) 0.1934(6) 0.0463(7) Uani d . 1 . . 0
H H14 0.5909 0.0047 0.2051 0.056 Uiso calc R 1 . . 0
C C15 0.62937(11) 0.07295(11) 0.0015(5) 0.0451(6) Uani d . 1 . . 0
H H15 0.6024 0.0597 -0.1175 0.054 Uiso calc R 1 . . 0
C C16 0.67646(10) 0.12540(10) -0.0156(4) 0.0374(5) Uani d . 1 . . 0
H H16 0.6811 0.1478 -0.1464 0.045 Uiso calc R 1 . . 0
C C17 0.88839(12) 0.11055(14) 0.1231(6) 0.0509(7) Uani d . 1 . . 0
H H17A 0.9112 0.0931 0.1098 0.076 Uiso calc R 1 . . 0
H H17B 0.8868 0.1260 -0.0264 0.076 Uiso calc R 1 . . 0
H H17C 0.8510 0.0829 0.1711 0.076 Uiso calc R 1 . . 0
C C18 0.97424(13) 0.25805(14) 0.8174(5) 0.0533(8) Uani d . 1 . . 0
H H18A 1.0064 0.2566 0.8759 0.080 Uiso calc R 1 . . 0
H H18B 0.9458 0.2455 0.9375 0.080 Uiso calc R 1 . . 0
H H18C 0.9854 0.2961 0.7738 0.080 Uiso calc R 1 . . 0
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
C4 O1 C17 . . 117.5(2) ?
C5 O2 C18 . . 117.1(2) ?
C10 O3 H3O . . 102(3) ?
C9 N1 C1 . . 111.16(18) ?
C9 N1 H1N . . 110(2) ?
C1 N1 H1N . . 112.6(19) ?
N1 C1 C2 . . 111.10(19) ?
N1 C1 C11 . . 112.09(18) ?
C2 C1 C11 . . 113.00(17) ?
N1 C1 H1 . . 106.7 ?
C2 C1 H1 . . 106.7 ?
C11 C1 H1 . . 106.7 ?
C7 C2 C3 . . 119.9(2) ?
C7 C2 C1 . . 121.3(2) ?
C3 C2 C1 . . 118.74(19) ?
C4 C3 C2 . . 120.6(2) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
O1 C4 C3 . . 125.5(2) ?
O1 C4 C5 . . 114.3(2) ?
C3 C4 C5 . . 120.2(2) ?
O2 C5 C6 . . 125.9(2) ?
O2 C5 C4 . . 115.1(2) ?
C6 C5 C4 . . 119.1(2) ?
C5 C6 C7 . . 121.2(2) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C2 C7 C6 . . 118.9(2) ?
C2 C7 C8 . . 121.7(2) ?
C6 C7 C8 . . 119.4(2) ?
C7 C8 C9 . . 111.3(2) ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8B . . 109.4 ?
C9 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
N1 C9 C8 . . 109.2(2) ?
N1 C9 C10 . . 108.7(2) ?
C8 C9 C10 . . 110.2(2) ?
N1 C9 H9 . . 109.6 ?
C8 C9 H9 . . 109.6 ?
C10 C9 H9 . . 109.6 ?
O3 C10 C9 . . 110.5(3) ?
O3 C10 H10A . . 109.6 ?
C9 C10 H10A . . 109.6 ?
O3 C10 H10B . . 109.6 ?
C9 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.1 ?
C16 C11 C12 . . 118.5(2) ?
C16 C11 C1 . . 119.09(19) ?
C12 C11 C1 . . 122.4(2) ?
C13 C12 C11 . . 120.8(3) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 120.5(2) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 120.0(2) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 119.5(3) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C11 C16 C15 . . 120.8(2) ?
C11 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
O1 C17 H17A . . 109.5 ?
O1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O2 C18 H18A . . 109.5 ?
O2 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O2 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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
O1 C4 . 1.368(3) ?
O1 C17 . 1.422(3) ?
O2 C5 . 1.362(3) ?
O2 C18 . 1.430(3) ?
O3 C10 . 1.357(5) ?
O3 H3O . 0.99(4) ?
N1 C9 . 1.477(3) ?
N1 C1 . 1.484(3) ?
N1 H1N . 0.97(3) ?
C1 C2 . 1.521(3) ?
C1 C11 . 1.524(3) ?
C1 H1 . 1.0000 ?
C2 C7 . 1.387(3) ?
C2 C3 . 1.399(3) ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.414(3) ?
C5 C6 . 1.370(4) ?
C6 C7 . 1.417(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.491(3) ?
C8 C9 . 1.502(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.528(4) ?
C9 H9 . 1.0000 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C16 . 1.390(3) ?
C11 C12 . 1.401(3) ?
C12 C13 . 1.375(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.387(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.386(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.401(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
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
O3 H3O O1W . 0.99(4) 1.95(4) 2.917(6) 164(5)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . -48.0(3) ?
C9 N1 C1 C11 . . . . 79.5(3) ?
N1 C1 C2 C7 . . . . 14.4(3) ?
C11 C1 C2 C7 . . . . -112.6(2) ?
N1 C1 C2 C3 . . . . -166.43(19) ?
C11 C1 C2 C3 . . . . 66.6(3) ?
C7 C2 C3 C4 . . . . -0.6(3) ?
C1 C2 C3 C4 . . . . -179.8(2) ?
C17 O1 C4 C3 . . . . -7.1(4) ?
C17 O1 C4 C5 . . . . 173.1(3) ?
C2 C3 C4 O1 . . . . 178.9(2) ?
C2 C3 C4 C5 . . . . -1.2(4) ?
C18 O2 C5 C6 . . . . 3.4(4) ?
C18 O2 C5 C4 . . . . -176.4(2) ?
O1 C4 C5 O2 . . . . 2.0(3) ?
C3 C4 C5 O2 . . . . -177.9(2) ?
O1 C4 C5 C6 . . . . -177.9(2) ?
C3 C4 C5 C6 . . . . 2.3(4) ?
O2 C5 C6 C7 . . . . 178.7(2) ?
C4 C5 C6 C7 . . . . -1.5(4) ?
C3 C2 C7 C6 . . . . 1.4(3) ?
C1 C2 C7 C6 . . . . -179.4(2) ?
C3 C2 C7 C8 . . . . -179.2(2) ?
C1 C2 C7 C8 . . . . -0.1(3) ?
C5 C6 C7 C2 . . . . -0.4(3) ?
C5 C6 C7 C8 . . . . -179.7(2) ?
C2 C7 C8 C9 . . . . 18.5(3) ?
C6 C7 C8 C9 . . . . -162.2(2) ?
C1 N1 C9 C8 . . . . 68.4(2) ?
C1 N1 C9 C10 . . . . -171.4(2) ?
C7 C8 C9 N1 . . . . -51.1(3) ?
C7 C8 C9 C10 . . . . -170.5(2) ?
N1 C9 C10 O3 . . . . 75.4(3) ?
C8 C9 C10 O3 . . . . -165.0(3) ?
N1 C1 C11 C16 . . . . 76.9(3) ?
C2 C1 C11 C16 . . . . -156.7(2) ?
N1 C1 C11 C12 . . . . -102.1(2) ?
C2 C1 C11 C12 . . . . 24.3(3) ?
C16 C11 C12 C13 . . . . 1.5(3) ?
C1 C11 C12 C13 . . . . -179.5(2) ?
C11 C12 C13 C14 . . . . 0.1(4) ?
C12 C13 C14 C15 . . . . -1.5(4) ?
C13 C14 C15 C16 . . . . 1.2(4) ?
C12 C11 C16 C15 . . . . -1.8(4) ?
C1 C11 C16 C15 . . . . 179.2(2) ?
C14 C15 C16 C11 . . . . 0.5(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656508
