#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:52:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153471.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7153471
loop_
_publ_author_name
'Selvakumar, Jayaraman'
'Makriyannis, Alexandros'
'Ramanathan, Chinnasamy Ramaraj'
_publ_section_title
;
 An unusual reactivity of BBr(3): Accessing tetrahydroisoquinoline units
 from N-phenethylimides.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4056
_journal_page_last               4058
_journal_paper_doi               10.1039/c0ob00269k
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.33
_chemical_melting_point          441
_chemical_name_common
;12b-Hydroxy-1,3-dimethoxy-5,12b-dihydro-6H-isoindolo(1,2-
a)isoquinolin-8-one
;
_chemical_name_systematic
;
12b-Hydroxy-1,3-dimethoxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 103.609(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.202(5)
_cell_length_b                   6.303(3)
_cell_length_c                   21.577(10)
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.60
_cell_measurement_theta_min      2.36
_cell_volume                     1480.7(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14321
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0716
_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)+(0.0968P)²+1.2570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1904
_refine_ls_wR_factor_ref         0.2052
_reflns_number_gt                2100
_reflns_number_total             2902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00269k.txt
_cod_data_source_block           epu103_m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1480.6(12)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153471
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O 0.79737(19) 0.1930(3) 0.13352(11) 0.0430(6) Uani 1 1 d .
H2 H 0.7691 0.3031 0.1444 0.065 Uiso 1 1 calc R
O3 O 0.6597(2) 0.2981(4) 0.23249(11) 0.0510(7) Uani 1 1 d .
N1 N 0.7697(2) -0.1747(4) 0.11994(12) 0.0350(6) Uani 1 1 d .
C16 C 0.7317(3) 0.0178(4) 0.14943(14) 0.0314(7) Uani 1 1 d .
O1 O 0.6848(2) -0.4684(3) 0.06490(11) 0.0519(7) Uani 1 1 d .
C10 C 0.5644(3) -0.1675(5) 0.08407(13) 0.0347(7) Uani 1 1 d .
C6 C 0.8459(3) -0.1739(4) 0.25012(14) 0.0339(7) Uani 1 1 d .
C9 C 0.6758(3) -0.2914(5) 0.08766(14) 0.0361(7) Uani 1 1 d .
C14 C 0.5077(3) 0.1790(5) 0.11262(15) 0.0395(7) Uani 1 1 d .
H14 H 0.5275 0.3086 0.1330 0.047 Uiso 1 1 calc R
C5 C 0.8820(3) -0.1915(5) 0.31595(15) 0.0419(8) Uani 1 1 d .
H5 H 0.9346 -0.3004 0.3342 0.050 Uiso 1 1 calc R
C4 C 0.8408(3) -0.0502(6) 0.35431(15) 0.0443(8) Uani 1 1 d .
C15 C 0.5951(3) 0.0209(4) 0.11751(13) 0.0316(7) Uani 1 1 d .
C2 C 0.7305(3) 0.1360(5) 0.26229(15) 0.0373(7) Uani 1 1 d .
C1 C 0.7675(2) -0.0110(4) 0.22175(14) 0.0312(7) Uani 1 1 d .
O4 O 0.8716(2) -0.0537(5) 0.41931(11) 0.0635(8) Uani 1 1 d .
C8 C 0.8916(3) -0.2559(5) 0.14501(16) 0.0419(8) Uani 1 1 d .
H8A H 0.9519 -0.1457 0.1447 0.050 Uiso 1 1 calc R
H8B H 0.9078 -0.3730 0.1190 0.050 Uiso 1 1 calc R
C13 C 0.3911(3) 0.1403(6) 0.07701(15) 0.0457(8) Uani 1 1 d .
H13 H 0.3319 0.2461 0.0732 0.055 Uiso 1 1 calc R
C7 C 0.9002(3) -0.3301(5) 0.21216(16) 0.0451(8) Uani 1 1 d .
H7A H 0.8576 -0.4646 0.2110 0.054 Uiso 1 1 calc R
H7B H 0.9858 -0.3532 0.2331 0.054 Uiso 1 1 calc R
C3 C 0.7646(3) 0.1171(6) 0.32747(15) 0.0452(8) Uani 1 1 d .
H3 H 0.7373 0.2147 0.3534 0.054 Uiso 1 1 calc R
C11 C 0.4469(3) -0.2086(5) 0.04925(15) 0.0437(8) Uani 1 1 d .
H11 H 0.4272 -0.3372 0.0282 0.052 Uiso 1 1 calc R
C12 C 0.3594(3) -0.0523(6) 0.04665(16) 0.0500(9) Uani 1 1 d .
H12 H 0.2787 -0.0765 0.0244 0.060 Uiso 1 1 calc R
C17 C 0.6092(4) 0.4437(6) 0.2700(2) 0.0621(11) Uani 1 1 d .
H17A H 0.5616 0.5488 0.2428 0.093 Uiso 1 1 calc R
H17B H 0.6745 0.5118 0.3003 0.093 Uiso 1 1 calc R
H17C H 0.5574 0.3685 0.2923 0.093 Uiso 1 1 calc R
C18 C 0.9457(4) -0.2273(8) 0.44924(19) 0.0776(14) Uani 1 1 d .
H18A H 0.9614 -0.2123 0.4947 0.116 Uiso 1 1 calc R
H18B H 1.0221 -0.2276 0.4364 0.116 Uiso 1 1 calc R
H18C H 0.9032 -0.3583 0.4366 0.116 Uiso 1 1 calc R
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
C2 O3 C17 118.7(3)
C9 N1 C8 124.1(3)
C9 N1 C16 113.9(2)
C8 N1 C16 118.3(2)
O2 C16 N1 108.5(2)
O2 C16 C15 113.9(2)
N1 C16 C15 100.2(2)
O2 C16 C1 108.3(2)
N1 C16 C1 108.0(2)
C15 C16 C1 117.2(2)
C11 C10 C15 122.1(3)
C11 C10 C9 128.6(3)
C15 C10 C9 109.0(3)
C5 C6 C1 120.6(3)
C5 C6 C7 116.7(3)
C1 C6 C7 122.6(3)
O1 C9 N1 125.2(3)
O1 C9 C10 127.8(3)
N1 C9 C10 106.9(2)
C13 C14 C15 118.6(3)
C4 C5 C6 120.6(3)
O4 C4 C5 124.9(3)
O4 C4 C3 114.9(3)
C5 C4 C3 120.1(3)
C14 C15 C10 119.4(3)
C14 C15 C16 131.4(3)
C10 C15 C16 108.9(2)
O3 C2 C3 122.8(3)
O3 C2 C1 115.3(3)
C3 C2 C1 122.0(3)
C6 C1 C2 117.4(3)
C6 C1 C16 121.5(2)
C2 C1 C16 120.9(3)
C4 O4 C18 117.1(3)
N1 C8 C7 108.2(3)
C14 C13 C12 121.6(3)
C6 C7 C8 112.3(3)
C2 C3 C4 119.1(3)
C10 C11 C12 117.8(3)
C11 C12 C13 120.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C16 1.413(3)
O3 C2 1.359(4)
O3 C17 1.426(4)
N1 C9 1.337(4)
N1 C8 1.440(4)
N1 C16 1.478(3)
C16 C15 1.523(4)
C16 C1 1.528(4)
O1 C9 1.233(4)
C10 C11 1.378(4)
C10 C15 1.390(4)
C10 C9 1.458(4)
C6 C5 1.387(4)
C6 C1 1.396(4)
C6 C7 1.498(4)
C14 C13 1.372(4)
C14 C15 1.384(4)
C5 C4 1.368(5)
C4 O4 1.363(4)
C4 C3 1.394(5)
C2 C3 1.373(4)
C2 C1 1.402(4)
O4 C18 1.432(5)
C8 C7 1.504(5)
C13 C12 1.386(5)
C11 C12 1.382(5)
