#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/90/2209093.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_2209093
loop_
_publ_author_name
'Roqué-Rosell, Nuria'
'Cironi, Pablo'
'Solans, Xavier'
'Albericio, Fernando'
'Álvarez, Mercedes'
_publ_section_title
;
 1-Hydroxy-6,7-dimethoxy-8-nitro-1,2,3,4-tetrahydroisoquinoline
;
_journal_coeditor_code           BT2065
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2285
_journal_page_last               o2287
_journal_paper_doi               10.1107/S160053680601693X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H14 N2 O5'
_chemical_formula_moiety         'C11 H14 N2 O5'
_chemical_formula_sum            'C11 H14 N2 O5'
_chemical_formula_weight         254.24
_chemical_name_systematic
;
1-Hydroxy-6,7-dimethoxy-8-nitro-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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.04(9)
_cell_angle_beta                 64.67(8)
_cell_angle_gamma                85.18(6)
_cell_formula_units_Z            2
_cell_length_a                   8.587(7)
_cell_length_b                   8.636(5)
_cell_length_c                   8.746(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      8
_cell_volume                     577.4(12)
_computing_cell_refinement       CAD-4/PC
_computing_data_collection       'CAD-4/PC (Kretschmar, 1996)'
_computing_data_reduction        'CFEO (Solans, 1978)'
_computing_molecular_graphics    'ORTEP3.2 (Brueggemann & Schmid, 1990)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3356
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0397
_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)+(0.0292P)²+0.1026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                2298
_reflns_number_total             3356
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2065.cif
_cod_data_source_block           IIIa
_cod_original_cell_volume        577.4(11)
_cod_database_code               2209093
_cod_database_fobs_code          2209093
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
O O1 0.4941(2) 0.28513(18) -0.00715(17) 0.0978(5) Uani d . 1
O O2 0.37603(17) 0.06798(18) 0.13553(15) 0.0835(4) Uani d . 1
O O3 0.22759(11) 0.38794(12) 0.64649(12) 0.0505(2) Uani d . 1
O O4 0.19553(11) 0.32718(12) 0.36703(12) 0.0498(2) Uani d . 1
O O5 0.85478(15) 0.19743(13) 0.00296(13) 0.0597(3) Uani d . 1
N N1 0.44888(14) 0.18835(16) 0.11867(14) 0.0482(3) Uani d . 1
N N2 0.88701(13) 0.00174(13) 0.20820(13) 0.0413(2) Uani d D 1
H H2N 0.8327(15) -0.0867(9) 0.2887(14) 0.050 Uiso d D 1
C C1 0.47871(15) 0.21569(14) 0.26640(15) 0.0361(3) Uani d . 1
C C2 0.63061(14) 0.16565(14) 0.28067(15) 0.0358(3) Uani d . 1
C C3 0.64549(15) 0.19049(14) 0.42675(15) 0.0373(3) Uani d . 1
C C4 0.51163(15) 0.26338(15) 0.55289(15) 0.0384(3) Uani d . 1
H H4 0.5229 0.2776 0.6507 0.046 Uiso calc R 1
C C5 0.36255(15) 0.31454(15) 0.53348(15) 0.0376(3) Uani d . 1
C C6 0.34426(14) 0.28961(15) 0.38693(15) 0.0375(3) Uani d . 1
C C7 0.77265(16) 0.08480(16) 0.14437(16) 0.0428(3) Uani d D 1
H H7 0.7195 0.0090 0.1103 0.051 Uiso calc R 1
C C8 0.94764(17) 0.0979(2) 0.29013(19) 0.0580(4) Uani d D 1
H H8 0.9946 0.1944 0.2132 0.070 Uiso calc R 1
H H8A 1.0392 0.0426 0.3151 0.070 Uiso calc R 1
C C9 0.80529(16) 0.13640(18) 0.45218(17) 0.0471(3) Uani d . 1
H H9 0.8423 0.2185 0.4918 0.056 Uiso calc R 1
H H9A 0.7791 0.0441 0.5394 0.056 Uiso calc R 1
C C10 0.1826(2) 0.4874(2) 0.2966(2) 0.0705(5) Uani d . 1
H H10 0.2813 0.5130 0.1898 0.085 Uiso calc R 1
H H10A 0.1780 0.5548 0.3749 0.085 Uiso calc R 1
H H10B 0.0798 0.5019 0.2776 0.085 Uiso calc R 1
C C11 0.2369(2) 0.41194(18) 0.79995(17) 0.0534(4) Uani d . 1
H H11 0.2311 0.3124 0.8707 0.064 Uiso calc R 1
H H11A 0.1423 0.4777 0.8606 0.064 Uiso calc R 1
H H11B 0.3436 0.4619 0.7716 0.064 Uiso calc R 1
H H5O 0.937(2) 0.154(2) -0.069(2) 0.067(5) 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
_geom_angle_publ_flag
C5 O3 C11 117.71(13) ?
C6 O4 C10 114.66(13) ?
C7 O5 H5O 107.9(12) ?
O1 N1 O2 124.10(15) yes
O1 N1 C1 119.21(16) yes
O2 N1 C1 116.68(15) yes
C7 N2 C8 112.20(12) yes
C7 N2 H2N 110.7(6) ?
C8 N2 H2N 108.0(6) ?
C6 C1 C2 124.02(13) ?
C6 C1 N1 115.14(13) yes
C2 C1 N1 120.82(13) yes
C1 C2 C3 117.14(13) ?
C1 C2 C7 121.40(13) ?
C3 C2 C7 121.45(13) ?
C2 C3 C4 120.69(13) ?
C2 C3 C9 119.97(13) ?
C4 C3 C9 119.33(13) ?
C5 C4 C3 120.79(13) ?
C5 C4 H4 119.6 ?
C3 C4 H4 119.6 ?
O3 C5 C4 125.21(13) ?
O3 C5 C6 115.33(13) ?
C4 C5 C6 119.46(13) ?
O4 C6 C1 120.05(13) ?
O4 C6 C5 121.95(13) ?
C1 C6 C5 117.88(13) ?
O5 C7 N2 112.82(14) ?
O5 C7 C2 108.22(14) ?
N2 C7 C2 111.12(14) ?
O5 C7 H7 108.2 ?
N2 C7 H7 108.2 ?
C2 C7 H7 108.2 ?
N2 C8 C9 111.03(15) ?
N2 C8 H8 109.4 ?
C9 C8 H8 109.4 ?
N2 C8 H8A 109.4 ?
C9 C8 H8A 109.4 ?
H8 C8 H8A 108.0 ?
C8 C9 C3 111.32(14) ?
C8 C9 H9 109.4 ?
C3 C9 H9 109.4 ?
C8 C9 H9A 109.4 ?
C3 C9 H9A 109.4 ?
H9 C9 H9A 108.0 ?
O4 C10 H10 109.5 ?
O4 C10 H10A 109.5 ?
H10 C10 H10A 109.5 ?
O4 C10 H10B 109.5 ?
H10 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
O3 C11 H11 109.5 ?
O3 C11 H11A 109.5 ?
H11 C11 H11A 109.5 ?
O3 C11 H11B 109.5 ?
H11 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.196(2) yes
O2 N1 1.2129(18) yes
O3 C5 1.355(2) ?
O3 C11 1.429(3) ?
O4 C6 1.3666(17) ?
O4 C10 1.430(2) ?
O5 C7 1.388(3) ?
O5 H5O 0.835(17) ?
N1 C1 1.480(3) yes
N2 C7 1.4151(19) yes
N2 C8 1.439(2) yes
N2 H2N 0.943(7) ?
C1 C6 1.385(2) ?
C1 C2 1.3891(18) ?
C2 C3 1.391(3) ?
C2 C7 1.516(3) ?
C3 C4 1.403(2) ?
C3 C9 1.5061(19) ?
C4 C5 1.3884(19) ?
C4 H4 0.9300 ?
C5 C6 1.410(3) ?
C7 H7 0.9800 ?
C8 C9 1.492(3) ?
C8 H8 0.9700 ?
C8 H8A 0.9700 ?
C9 H9 0.9700 ?
C9 H9A 0.9700 ?
C10 H10 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C11 H11 0.9600 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
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
_geom_hbond_publ_flag
O5 H5O N2 2_755 0.832(17) 2.056(18) 2.870(5) 166.2(17) yes
