#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/29/2212926.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_2212926
loop_
_publ_author_name
'Zhi-Hong Zou'
'Yong Ling'
'Wen-Long Huang'
_publ_section_title
2-(2-Chloroacetyl)-6,7-dimethoxy-1-(phenoxymethyl)-1,2,3,4-tetrahydroisoquinoline
_journal_coeditor_code           HK2202
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1596
_journal_page_last               o1597
_journal_paper_doi               10.1107/S1600536807009476
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H22 Cl N O4'
_chemical_formula_moiety         'C20 H22 Cl N O4'
_chemical_formula_sum            'C20 H22 Cl N O4'
_chemical_formula_weight         375.84
_chemical_melting_point          400(2)
_chemical_name_systematic
;
2-(2-Chloroacetyl)-6,7-dimethoxy-1-(phenoxymethyl)-1,2,3,4-
tetrahydroisoquinoline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                93.69(3)
_cell_angle_beta                 107.82(3)
_cell_angle_gamma                111.10(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7110(17)
_cell_length_b                   9.6550(19)
_cell_length_c                   12.668(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     927.9(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3881
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.9133
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.264
_refine_ls_extinction_coef       0.036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0539
_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)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1674
_reflns_number_gt                2586
_reflns_number_total             3629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2202.cif
_cod_data_source_block           I
_cod_database_code               2212926
_cod_database_fobs_code          2212926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl 0.17710(11) 0.51102(10) 0.12183(6) 0.0824(3) Uani d . 1
O O1 0.7628(2) 1.0018(2) 0.89619(14) 0.0602(5) Uani d . 1
O O2 0.4500(2) 0.8493(2) 0.89564(13) 0.0535(5) Uani d . 1
O O3 0.1033(2) 0.35586(19) 0.35191(15) 0.0581(5) Uani d . 1
O O4 -0.0327(2) 0.63631(17) 0.35189(13) 0.0493(4) Uani d . 1
N N 0.2909(2) 0.6032(2) 0.39857(15) 0.0426(5) Uani d . 1
C C1 0.9280(4) 1.1052(4) 0.8959(3) 0.0827(10) Uani d . 1
H H1A 0.9999 1.1621 0.9711 0.124 Uiso calc R 1
H H1B 0.9091 1.1731 0.8462 0.124 Uiso calc R 1
H H1C 0.9862 1.0499 0.8702 0.124 Uiso calc R 1
C C2 0.2767(3) 0.7835(3) 0.8983(2) 0.0526(6) Uani d . 1
H H2A 0.2803 0.8056 0.9742 0.079 Uiso calc R 1
H H2B 0.2296 0.6759 0.8730 0.079 Uiso calc R 1
H H2C 0.2034 0.8248 0.8495 0.079 Uiso calc R 1
C C3 0.6431(3) 0.9126(3) 0.79509(18) 0.0434(5) Uani d . 1
C C4 0.4719(3) 0.8296(2) 0.79472(17) 0.0389(5) Uani d . 1
C C5 0.3433(3) 0.7380(2) 0.69643(18) 0.0387(5) Uani d . 1
H H5A 0.2309 0.6825 0.6961 0.046 Uiso calc R 1
C C6 0.3793(3) 0.7270(2) 0.59609(17) 0.0369(5) Uani d . 1
C C7 0.2268(3) 0.6345(2) 0.48847(17) 0.0387(5) Uani d . 1
H H7A 0.1583 0.5380 0.5042 0.046 Uiso calc R 1
C C8 0.4289(3) 0.7347(3) 0.38480(19) 0.0496(6) Uani d . 1
H H8A 0.3863 0.8140 0.3692 0.059 Uiso calc R 1
H H8B 0.4585 0.7064 0.3212 0.059 Uiso calc R 1
C C9 0.5911(3) 0.7933(3) 0.4911(2) 0.0538(6) Uani d . 1
H H9A 0.6509 0.7252 0.4954 0.065 Uiso calc R 1
H H9B 0.6709 0.8918 0.4873 0.065 Uiso calc R 1
C C10 0.5468(3) 0.8067(2) 0.59637(18) 0.0412(5) Uani d . 1
C C11 0.6780(3) 0.8992(3) 0.69732(19) 0.0456(6) Uani d . 1
H H11A 0.7911 0.9527 0.6980 0.055 Uiso calc R 1
C C12 0.2730(4) 0.4371(3) 0.2362(2) 0.0630(7) Uani d . 1
H H12A 0.2382 0.3295 0.2120 0.076 Uiso calc R 1
H H12B 0.4001 0.4860 0.2603 0.076 Uiso calc R 1
C C13 0.2154(3) 0.4626(3) 0.33435(19) 0.0444(5) Uani d . 1
C C14 0.1106(3) 0.7202(2) 0.45327(18) 0.0428(5) Uani d . 1
H H14A 0.0665 0.7361 0.5126 0.051 Uiso calc R 1
H H14B 0.1782 0.8184 0.4413 0.051 Uiso calc R 1
C C15 -0.1337(3) 0.7090(2) 0.29734(19) 0.0421(5) Uani d . 1
C C16 -0.1182(3) 0.8506(3) 0.3409(2) 0.0476(6) Uani d . 1
H H16A -0.0383 0.9014 0.4129 0.057 Uiso calc R 1
C C17 -0.2221(3) 0.9159(3) 0.2769(2) 0.0565(7) Uani d . 1
H H17A -0.2110 1.0112 0.3063 0.068 Uiso calc R 1
C C18 -0.3413(4) 0.8430(3) 0.1708(2) 0.0625(7) Uani d . 1
H H18A -0.4098 0.8884 0.1278 0.075 Uiso calc R 1
C C19 -0.3577(4) 0.7018(3) 0.1292(2) 0.0676(8) Uani d . 1
H H19A -0.4385 0.6510 0.0574 0.081 Uiso calc R 1
C C20 -0.2573(3) 0.6348(3) 0.1914(2) 0.0596(7) Uani d . 1
H H20A -0.2721 0.5381 0.1623 0.072 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C3 O1 C1 117.2(2) ?
C4 O2 C2 118.15(18) ?
C15 O4 C14 117.11(17) ?
C13 N C8 126.21(19) yes
C13 N C7 119.07(18) yes
C8 N C7 114.65(18) yes
O1 C1 H1A 109.5 ?
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O2 C2 H2A 109.5 ?
O2 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
O2 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
O1 C3 C11 124.9(2) yes
O1 C3 C4 115.6(2) yes
C11 C3 C4 119.5(2) ?
O2 C4 C5 125.3(2) yes
O2 C4 C3 115.29(19) yes
C5 C4 C3 119.43(19) ?
C4 C5 C6 120.7(2) ?
C4 C5 H5A 119.6 ?
C6 C5 H5A 119.6 ?
C10 C6 C5 119.99(19) ?
C10 C6 C7 122.17(19) ?
C5 C6 C7 117.71(18) ?
N C7 C14 111.32(17) yes
N C7 C6 110.82(17) yes
C14 C7 C6 108.49(17) ?
N C7 H7A 108.7 ?
C14 C7 H7A 108.7 ?
C6 C7 H7A 108.7 ?
N C8 C9 110.24(19) yes
N C8 H8A 109.6 ?
C9 C8 H8A 109.6 ?
N C8 H8B 109.6 ?
C9 C8 H8B 109.6 ?
H8A C8 H8B 108.1 ?
C10 C9 C8 112.1(2) ?
C10 C9 H9A 109.2 ?
C8 C9 H9A 109.2 ?
C10 C9 H9B 109.2 ?
C8 C9 H9B 109.2 ?
H9A C9 H9B 107.9 ?
C6 C10 C11 119.0(2) ?
C6 C10 C9 121.3(2) ?
C11 C10 C9 119.7(2) ?
C3 C11 C10 121.4(2) ?
C3 C11 H11A 119.3 ?
C10 C11 H11A 119.3 ?
C13 C12 Cl 110.64(18) ?
C13 C12 H12A 109.5 ?
Cl C12 H12A 109.5 ?
C13 C12 H12B 109.5 ?
Cl C12 H12B 109.5 ?
H12A C12 H12B 108.1 ?
O3 C13 N 123.1(2) ?
O3 C13 C12 119.0(2) ?
N C13 C12 117.9(2) ?
O4 C14 C7 109.56(18) ?
O4 C14 H14A 109.8 ?
C7 C14 H14A 109.8 ?
O4 C14 H14B 109.8 ?
C7 C14 H14B 109.8 ?
H14A C14 H14B 108.2 ?
O4 C15 C20 116.9(2) ?
O4 C15 C16 124.4(2) ?
C20 C15 C16 118.7(2) ?
C17 C16 C15 119.6(2) ?
C17 C16 H16A 120.2 ?
C15 C16 H16A 120.2 ?
C18 C17 C16 121.3(2) ?
C18 C17 H17A 119.4 ?
C16 C17 H17A 119.4 ?
C19 C18 C17 118.7(2) ?
C19 C18 H18A 120.6 ?
C17 C18 H18A 120.6 ?
C20 C19 C18 120.9(2) ?
C20 C19 H19A 119.5 ?
C18 C19 H19A 119.5 ?
C19 C20 C15 120.8(2) ?
C19 C20 H20A 119.6 ?
C15 C20 H20A 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C12 1.769(3) ?
O1 C3 1.365(3) yes
O1 C1 1.427(3) yes
O2 C4 1.360(3) yes
O2 C2 1.424(3) yes
O3 C13 1.226(3) yes
O4 C15 1.371(3) yes
O4 C14 1.421(3) yes
N C13 1.351(3) yes
N C8 1.465(3) yes
N C7 1.472(3) yes
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 C11 1.371(3) ?
C3 C4 1.415(3) ?
C4 C5 1.371(3) ?
C5 C6 1.406(3) ?
C5 H5A 0.9300 ?
C6 C10 1.381(3) ?
C6 C7 1.517(3) ?
C7 C14 1.511(3) ?
C7 H7A 0.9800 ?
C8 C9 1.514(3) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.508(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.401(3) ?
C11 H11A 0.9300 ?
C12 C13 1.512(3) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C20 1.382(3) ?
C15 C16 1.384(3) ?
C16 C17 1.378(3) ?
C16 H16A 0.9300 ?
C17 C18 1.371(4) ?
C17 H17A 0.9300 ?
C18 C19 1.370(4) ?
C18 H18A 0.9300 ?
C19 C20 1.362(4) ?
C19 H19A 0.9300 ?
C20 H20A 0.9300 ?
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
_geom_torsion_publ_flag
C1 O1 C3 C11 9.8(4) ?
C1 O1 C3 C4 -170.2(2) ?
C2 O2 C4 C5 -7.2(3) ?
C2 O2 C4 C3 172.7(2) ?
O1 C3 C4 O2 -0.4(3) ?
C11 C3 C4 O2 179.6(2) ?
O1 C3 C4 C5 179.5(2) ?
C11 C3 C4 C5 -0.4(3) ?
O2 C4 C5 C6 179.2(2) ?
C3 C4 C5 C6 -0.7(3) ?
C4 C5 C6 C10 1.3(3) ?
C4 C5 C6 C7 -174.68(19) ?
C13 N C7 C14 -102.9(2) ?
C8 N C7 C14 74.3(2) ?
C13 N C7 C6 136.2(2) ?
C8 N C7 C6 -46.6(2) yes
C10 C6 C7 N 18.0(3) yes
C5 C6 C7 N -166.17(18) ?
C10 C6 C7 C14 -104.5(2) ?
C5 C6 C7 C14 71.3(2) ?
C13 N C8 C9 -120.2(2) ?
C7 N C8 C9 62.9(3) yes
N C8 C9 C10 -46.7(3) yes
C5 C6 C10 C11 -0.8(3) ?
C7 C6 C10 C11 175.0(2) ?
C5 C6 C10 C9 177.9(2) ?
C7 C6 C10 C9 -6.3(3) yes
C8 C9 C10 C6 20.5(3) yes
C8 C9 C10 C11 -160.8(2) ?
O1 C3 C11 C10 -179.0(2) ?
C4 C3 C11 C10 0.9(4) ?
C6 C10 C11 C3 -0.3(4) ?
C9 C10 C11 C3 -179.1(2) ?
C8 N C13 O3 178.1(2) ?
C7 N C13 O3 -5.1(3) ?
C8 N C13 C12 -2.0(3) ?
C7 N C13 C12 174.82(19) ?
Cl C12 C13 O3 103.5(2) ?
Cl C12 C13 N -76.5(3) ?
C15 O4 C14 C7 -168.83(17) ?
N C7 C14 O4 57.3(2) ?
C6 C7 C14 O4 179.46(17) ?
C14 O4 C15 C20 171.4(2) ?
C14 O4 C15 C16 -7.9(3) ?
O4 C15 C16 C17 177.5(2) ?
C20 C15 C16 C17 -1.8(3) ?
C15 C16 C17 C18 0.3(4) ?
C16 C17 C18 C19 0.8(4) ?
C17 C18 C19 C20 -0.3(4) ?
C18 C19 C20 C15 -1.3(5) ?
O4 C15 C20 C19 -177.0(2) ?
C16 C15 C20 C19 2.4(4) ?
