#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230380.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_2230380
loop_
_publ_author_name
'Naicker, Tricia'
'Govender, Thavendran'
'Kruger, Hendrik G.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 (1S,3S)-Methyl
 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
;
_journal_coeditor_code           IS2714
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1501
_journal_paper_doi               10.1107/S1600536811018782
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H21 N O4'
_chemical_formula_moiety         'C19 H21 N O4'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37
_chemical_melting_point          371
_chemical_name_systematic
;
(1S,3S)-Methyl
6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.475(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3841(3)
_cell_length_b                   6.3453(2)
_cell_length_c                   14.2048(4)
_cell_measurement_reflns_used    4184
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.18
_cell_volume                     843.25(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ 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  0.0095
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4184
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.125
_refine_ls_extinction_coef       0.014(4)
_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     222
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0302
_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)+(0.0478P)²+0.1004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                2138
_reflns_number_total             2275
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2714.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2230380
_cod_database_fobs_code          2230380
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.32761(13) 0.8193(2) 0.52227(9) 0.0421(3) Uani d . 1 1 . .
O O2 0.14691(13) 0.5304(2) 0.46573(8) 0.0377(3) Uani d . 1 1 . .
O O3 0.39059(11) -0.1210(2) 0.96117(8) 0.0372(3) Uani d . 1 1 . .
O O4 0.15273(11) -0.0802(2) 0.93763(8) 0.0359(3) Uani d . 1 1 . .
N N1 0.44475(13) 0.2219(2) 0.85516(9) 0.0286(3) Uani d D 1 1 . .
H H1N 0.4969(18) 0.214(4) 0.9118(11) 0.033(5) Uiso d D 1 1 . .
C C1 0.45806(15) 0.4396(3) 0.82212(10) 0.0276(3) Uani d . 1 1 . .
H H1 0.4271 0.5382 0.8715 0.033 Uiso calc R 1 1 . .
C C2 0.36095(14) 0.4684(2) 0.73185(10) 0.0260(3) Uani d . 1 1 . .
C C3 0.38575(16) 0.6398(3) 0.67243(11) 0.0303(3) Uani d . 1 1 . .
H H3 0.4558 0.7420 0.6921 0.036 Uiso calc R 1 1 . .
C C4 0.30923(16) 0.6610(3) 0.58571(11) 0.0309(3) Uani d . 1 1 . .
C C5 0.20784(15) 0.5077(3) 0.55602(10) 0.0299(3) Uani d . 1 1 . .
C C6 0.17693(14) 0.3466(3) 0.61690(10) 0.0273(3) Uani d . 1 1 . .
H H6 0.1036 0.2485 0.5984 0.033 Uiso calc R 1 1 . .
C C7 0.25316(14) 0.3266(2) 0.70613(10) 0.0250(3) Uani d . 1 1 . .
C C8 0.21706(15) 0.1462(3) 0.76978(10) 0.0274(3) Uani d . 1 1 . .
H H8A 0.2446 0.0110 0.7415 0.033 Uiso calc R 1 1 . .
H H8B 0.1127 0.1433 0.7759 0.033 Uiso calc R 1 1 . .
C C9 0.29613(15) 0.1715(3) 0.86760(10) 0.0259(3) Uani d . 1 1 . .
H H9 0.2524 0.2909 0.9011 0.031 Uiso calc R 1 1 . .
C C10 0.28876(15) -0.0258(3) 0.92677(10) 0.0273(3) Uani d . 1 1 . .
C C11 0.1344(2) -0.2585(3) 0.99879(13) 0.0423(4) Uani d . 1 1 . .
H H11A 0.0322 -0.2859 1.0025 0.063 Uiso calc R 1 1 . .
H H11B 0.1788 -0.2277 1.0621 0.063 Uiso calc R 1 1 . .
H H11C 0.1799 -0.3829 0.9733 0.063 Uiso calc R 1 1 . .
C C12 0.61296(15) 0.4843(3) 0.80537(10) 0.0291(3) Uani d . 1 1 . .
C C13 0.68782(16) 0.3487(3) 0.74980(11) 0.0374(4) Uani d . 1 1 . .
H H13 0.6419 0.2270 0.7229 0.045 Uiso calc R 1 1 . .
C C14 0.82974(17) 0.3906(4) 0.73342(12) 0.0426(4) Uani d . 1 1 . .
H H14 0.8798 0.2980 0.6951 0.051 Uiso calc R 1 1 . .
C C15 0.89763(17) 0.5663(4) 0.77280(13) 0.0431(4) Uani d . 1 1 . .
H H15 0.9951 0.5924 0.7631 0.052 Uiso calc R 1 1 . .
C C16 0.82347(18) 0.7041(3) 0.82631(13) 0.0419(4) Uani d . 1 1 . .
H H16 0.8695 0.8269 0.8520 0.050 Uiso calc R 1 1 . .
C C17 0.68109(16) 0.6639(3) 0.84278(11) 0.0339(3) Uani d . 1 1 . .
H H17 0.6307 0.7594 0.8796 0.041 Uiso calc R 1 1 . .
C C18 0.43336(19) 0.9743(3) 0.54802(15) 0.0450(4) Uani d . 1 1 . .
H H18A 0.4362 1.0782 0.4972 0.067 Uiso calc R 1 1 . .
H H18B 0.5270 0.9062 0.5585 0.067 Uiso calc R 1 1 . .
H H18C 0.4097 1.0450 0.6061 0.067 Uiso calc R 1 1 . .
C C19 0.0553(2) 0.3649(3) 0.43094(12) 0.0480(5) Uani d . 1 1 . .
H H19A 0.0173 0.3981 0.3664 0.072 Uiso calc R 1 1 . .
H H19B -0.0238 0.3498 0.4715 0.072 Uiso calc R 1 1 . .
H H19C 0.1094 0.2328 0.4308 0.072 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 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 C18 . . 117.28(14) ?
C5 O2 C19 . . 116.41(13) ?
C10 O4 C11 . . 115.40(13) ?
C9 N1 C1 . . 110.63(12) ?
C9 N1 H1N . . 109.5(12) ?
C1 N1 H1N . . 106.5(15) ?
N1 C1 C12 . . 109.42(13) ?
N1 C1 C2 . . 108.75(12) ?
C12 C1 C2 . . 111.26(12) ?
N1 C1 H1 . . 109.1 ?
C12 C1 H1 . . 109.1 ?
C2 C1 H1 . . 109.1 ?
C7 C2 C3 . . 119.79(13) ?
C7 C2 C1 . . 121.43(13) ?
C3 C2 C1 . . 118.75(13) ?
C4 C3 C2 . . 120.72(14) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
O1 C4 C3 . . 125.04(15) ?
O1 C4 C5 . . 115.36(14) ?
C3 C4 C5 . . 119.55(14) ?
O2 C5 C6 . . 124.75(14) ?
O2 C5 C4 . . 115.61(14) ?
C6 C5 C4 . . 119.64(13) ?
C5 C6 C7 . . 120.76(14) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C2 C7 C6 . . 119.20(13) ?
C2 C7 C8 . . 121.88(12) ?
C6 C7 C8 . . 118.89(13) ?
C7 C8 C9 . . 110.34(12) ?
C7 C8 H8A . . 109.6 ?
C9 C8 H8A . . 109.6 ?
C7 C8 H8B . . 109.6 ?
C9 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
N1 C9 C10 . . 109.60(12) ?
N1 C9 C8 . . 108.29(11) ?
C10 C9 C8 . . 112.19(12) ?
N1 C9 H9 . . 108.9 ?
C10 C9 H9 . . 108.9 ?
C8 C9 H9 . . 108.9 ?
O3 C10 O4 . . 123.84(15) ?
O3 C10 C9 . . 124.95(14) ?
O4 C10 C9 . . 111.20(12) ?
O4 C11 H11A . . 109.5 ?
O4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 119.00(14) ?
C17 C12 C1 . . 120.67(14) ?
C13 C12 C1 . . 120.31(14) ?
C12 C13 C14 . . 120.43(18) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 120.18(18) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 119.84(16) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.37(18) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C12 C17 C16 . . 120.14(16) ?
C12 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
O1 C18 H18A . . 109.5 ?
O1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O2 C19 H19A . . 109.5 ?
O2 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O2 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 . 1.3696(19) ?
O1 C18 . 1.424(2) ?
O2 C5 . 1.3704(18) ?
O2 C19 . 1.421(2) ?
O3 C10 . 1.2017(18) ?
O4 C10 . 1.3429(18) ?
O4 C11 . 1.445(2) ?
N1 C9 . 1.4552(18) ?
N1 C1 . 1.467(2) ?
N1 H1N . 0.909(14) ?
C1 C12 . 1.5178(19) ?
C1 C2 . 1.525(2) ?
C1 H1 . 1.0000 ?
C2 C7 . 1.381(2) ?
C2 C3 . 1.407(2) ?
C3 C4 . 1.383(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.403(2) ?
C5 C6 . 1.384(2) ?
C6 C7 . 1.4118(18) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.513(2) ?
C8 C9 . 1.5317(19) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.512(2) ?
C9 H9 . 1.0000 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C17 . 1.392(2) ?
C12 C13 . 1.394(2) ?
C13 C14 . 1.395(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.380(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.382(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.398(2) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 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
N1 H1N O3 2_657 0.910(16) 2.2741(18) 3.0918(17) 149(2)
C1 H1 O3 1_565 1.00 2.55 3.503(2) 160
C19 H19B O2 2_546 0.98 2.53 3.270(2) 132
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 C12 . . . . -177.34(12) ?
C9 N1 C1 C2 . . . . -55.63(14) ?
N1 C1 C2 C7 . . . . 16.42(18) ?
C12 C1 C2 C7 . . . . 137.00(14) ?
N1 C1 C2 C3 . . . . -161.44(13) ?
C12 C1 C2 C3 . . . . -40.86(19) ?
C7 C2 C3 C4 . . . . -4.0(2) ?
C1 C2 C3 C4 . . . . 173.89(14) ?
C18 O1 C4 C3 . . . . -0.3(2) ?
C18 O1 C4 C5 . . . . -177.71(14) ?
C2 C3 C4 O1 . . . . -178.59(14) ?
C2 C3 C4 C5 . . . . -1.2(2) ?
C19 O2 C5 C6 . . . . -5.8(2) ?
C19 O2 C5 C4 . . . . 173.61(15) ?
O1 C4 C5 O2 . . . . 3.6(2) ?
C3 C4 C5 O2 . . . . -174.04(14) ?
O1 C4 C5 C6 . . . . -177.03(13) ?
C3 C4 C5 C6 . . . . 5.4(2) ?
O2 C5 C6 C7 . . . . 175.00(14) ?
C4 C5 C6 C7 . . . . -4.4(2) ?
C3 C2 C7 C6 . . . . 5.0(2) ?
C1 C2 C7 C6 . . . . -172.82(13) ?
C3 C2 C7 C8 . . . . -176.77(13) ?
C1 C2 C7 C8 . . . . 5.4(2) ?
C5 C6 C7 C2 . . . . -0.9(2) ?
C5 C6 C7 C8 . . . . -179.14(14) ?
C2 C7 C8 C9 . . . . 9.86(19) ?
C6 C7 C8 C9 . . . . -171.91(13) ?
C1 N1 C9 C10 . . . . -163.99(11) ?
C1 N1 C9 C8 . . . . 73.33(15) ?
C7 C8 C9 N1 . . . . -46.80(16) ?
C7 C8 C9 C10 . . . . -167.89(11) ?
C11 O4 C10 O3 . . . . 3.2(2) ?
C11 O4 C10 C9 . . . . -175.80(13) ?
N1 C9 C10 O3 . . . . 2.7(2) ?
C8 C9 C10 O3 . . . . 123.00(16) ?
N1 C9 C10 O4 . . . . -178.38(12) ?
C8 C9 C10 O4 . . . . -58.05(15) ?
N1 C1 C12 C17 . . . . -130.54(15) ?
C2 C1 C12 C17 . . . . 109.27(16) ?
N1 C1 C12 C13 . . . . 51.37(18) ?
C2 C1 C12 C13 . . . . -68.82(19) ?
C17 C12 C13 C14 . . . . 1.2(3) ?
C1 C12 C13 C14 . . . . 179.29(16) ?
C12 C13 C14 C15 . . . . 0.5(3) ?
C13 C14 C15 C16 . . . . -1.9(3) ?
C14 C15 C16 C17 . . . . 1.6(3) ?
C13 C12 C17 C16 . . . . -1.4(2) ?
C1 C12 C17 C16 . . . . -179.55(15) ?
C15 C16 C17 C12 . . . . 0.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9704734
