#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/07/2010774.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_2010774
loop_
_publ_author_name
'Şimşek, Rahime'
'Linden, Anthony'
'Şafak, Cihat'
_publ_section_title
(+-)-9-(2-Bromophenyl)-7,7-dimethyl-1,3,4,5,6,7,8,9-octahydrofuro[3,4-b]quinoline-1,8-dione
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              351
_journal_page_last               353
_journal_paper_doi               10.1107/S0108270199015255
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C19 H18 Br N O3'
_chemical_formula_sum            'C19 H18 Br N O3'
_chemical_formula_weight         388.26
_chemical_melting_point          575
_chemical_name_systematic
;
(+-)-9-(2-Bromophenyl)-7,7-dimethyl-1,3,4,5,6,7,8,9-octahydrofuro[3,4-
b]quinoline-1,8-dione
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.11(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.724(5)
_cell_length_b                   10.911(4)
_cell_length_c                   14.218(6)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      18.5
_cell_volume                     1672.8(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1991)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      180.0(10)
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .091
_diffrn_reflns_av_sigmaI/netI    .127
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4239
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_T_max  .609
_exptl_absorpt_correction_T_min  .536
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .21
_refine_diff_density_max         .866
_refine_diff_density_min         -.737
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .967
_refine_ls_R_factor_all          .160
_refine_ls_R_factor_gt           .059
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0831P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .165
_reflns_number_gt                2018
_reflns_number_total             3842
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1350.cif
_cod_data_source_block           I
_cod_original_cell_volume        1672.9(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2010774
_cod_database_fobs_code          2010774
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_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_type_symbol
Br1 .07276(7) .82218(5) .10441(5) .0513(2) Uani d . 1 . . Br
O2 .2878(4) .5733(3) .1869(3) .0421(10) Uani d . 1 . . O
O9 -.1074(3) .5731(3) -.2880(2) .0301(8) Uani d . 1 . . O
O10 -.1004(3) .7311(3) -.1864(3) .0322(8) Uani d . 1 . . O
N1 .1497(4) .3785(4) -.1352(3) .0269(9) Uani d . 1 . . N
H1 .1602 .3196 -.1734 .046(17) Uiso calc R 1 . . H
C2 .0571(4) .4626(4) -.1763(4) .0235(10) Uani d . 1 . . C
C3 .0428(4) .5611(4) -.1248(4) .0246(10) Uani d . 1 . . C
C4 .1284(4) .5909(4) -.0163(3) .0218(10) Uani d . 1 . . C
H4 .0780 .5997 .0260 .026 Uiso calc R 1 . . H
C4a .2187(4) .4835(4) .0254(3) .0244(11) Uani d . 1 . . C
C5 .2987(5) .4888(4) .1343(4) .0274(11) Uani d . 1 . . C
C6 .3999(5) .3911(5) .1806(4) .0313(12) Uani d . 1 . . C
C7 .3605(5) .2702(5) .1218(4) .0322(12) Uani d . 1 . . C
H7a .4314 .2126 .1463 .039 Uiso calc R 1 . . H
H7B .2925 .2336 .1372 .039 Uiso calc R 1 . . H
C8 .3175(5) .2846(5) .0068(4) .0332(12) Uani d . 1 . . C
H8a .3902 .3005 -.0104 .040 Uiso calc R 1 . . H
H8B .2785 .2073 -.0270 .040 Uiso calc R 1 . . H
C8a .2267(4) .3871(4) -.0330(4) .0238(11) Uani d . 1 . . C
C9 -.0424(5) .4580(4) -.2804(4) .0288(11) Uani d . 1 . . C
H9a -.0072 .4524 -.3331 .035 Uiso calc R 1 . . H
H9B -.0982 .3874 -.2877 .035 Uiso calc R 1 . . H
C10 -.0583(4) .6308(5) -.1962(4) .0273(11) Uani d . 1 . . C
C11 .1971(4) .7123(4) -.0128(3) .0225(10) Uani d . 1 . . C
C12 .1829(5) .8182(5) .0349(3) .0275(11) Uani d . 1 . . C
C13 .2431(5) .9268(5) .0325(4) .0309(12) Uani d . 1 . . C
H13 .2311 .9977 .0663 .037 Uiso calc R 1 . . H
C14 .3212(5) .9307(5) -.0198(4) .0341(12) Uani d . 1 . . C
H14 .3641 1.0040 -.0214 .041 Uiso calc R 1 . . H
C15 .3360(5) .8261(5) -.0698(4) .0343(12) Uani d . 1 . . C
H15 .3878 .8286 -.1071 .041 Uiso calc R 1 . . H
C16 .2758(5) .7187(4) -.0656(4) .0268(11) Uani d . 1 . . C
H16 .2881 .6477 -.0992 .032 Uiso calc R 1 . . H
C17 .5194(5) .4417(5) .1740(4) .0429(14) Uani d . 1 . . C
H17a .5393 .5216 .2080 .064 Uiso calc R 1 . . H
H17B .5069 .4509 .1020 .064 Uiso calc R 1 . . H
H17C .5880 .3846 .2076 .064 Uiso calc R 1 . . H
C18 .4222(5) .3685(6) .2929(4) .0409(14) Uani d . 1 . . C
H18a .3464 .3359 .2971 .061 Uiso calc R 1 . . H
H18B .4446 .4458 .3308 .061 Uiso calc R 1 . . H
H18C .4897 .3093 .3226 .061 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H .0000 .0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
Br Br -.2901 2.4595
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N .0061 .0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O .0106 .0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 -3
-2 0 -2
-2 1 -2
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
C10 O9 C9 108.5(4) ?
C2 N1 C8a 119.1(4) ?
C2 N1 H1 120.5 ?
C8a N1 H1 120.5 ?
C3 C2 N1 123.5(5) ?
C3 C2 C9 110.6(4) ?
N1 C2 C9 125.9(4) ?
C2 C3 C10 106.4(4) ?
C2 C3 C4 123.5(4) ?
C10 C3 C4 129.8(4) ?
C3 C4 C4a 108.2(4) ?
C3 C4 C11 110.3(4) ?
C4a C4 C11 111.8(4) ?
C3 C4 H4 108.8 ?
C4a C4 H4 108.8 ?
C11 C4 H4 108.8 ?
C8a C4a C5 120.4(4) ?
C8a C4a C4 123.7(4) ?
C5 C4a C4 115.9(4) ?
O2 C5 C4a 119.9(5) ?
O2 C5 C6 120.6(4) ?
C4a C5 C6 119.5(4) ?
C7 C6 C18 108.8(4) ?
C7 C6 C5 110.3(4) ?
C18 C6 C5 110.2(4) ?
C7 C6 C17 111.1(4) ?
C18 C6 C17 109.5(4) ?
C5 C6 C17 107.0(4) ?
C8 C7 C6 113.6(4) ?
C8 C7 H7a 108.8 ?
C6 C7 H7a 108.8 ?
C8 C7 H7B 108.8 ?
C6 C7 H7B 108.8 ?
H7a C7 H7B 107.7 ?
C8a C8 C7 111.8(4) ?
C8a C8 H8a 109.3 ?
C7 C8 H8a 109.3 ?
C8a C8 H8B 109.3 ?
C7 C8 H8B 109.3 ?
H8a C8 H8B 107.9 ?
C4a C8a N1 121.3(4) ?
C4a C8a C8 123.7(4) ?
N1 C8a C8 115.0(4) ?
O9 C9 C2 103.3(4) ?
O9 C9 H9a 111.1 ?
C2 C9 H9a 111.1 ?
O9 C9 H9B 111.1 ?
C2 C9 H9B 111.1 ?
H9a C9 H9B 109.1 ?
O10 C10 O9 118.9(4) yes
O10 C10 C3 130.2(5) yes
O9 C10 C3 110.8(4) ?
C12 C11 C16 116.9(4) ?
C12 C11 C4 124.9(4) ?
C16 C11 C4 118.1(4) ?
C11 C12 C13 122.8(4) ?
C11 C12 Br1 120.6(4) ?
C13 C12 Br1 116.6(4) ?
C12 C13 C14 119.2(5) ?
C12 C13 H13 120.4 ?
C14 C13 H13 120.4 ?
C13 C14 C15 119.3(5) ?
C13 C14 H14 120.3 ?
C15 C14 H14 120.3 ?
C16 C15 C14 120.4(5) ?
C16 C15 H15 119.8 ?
C14 C15 H15 119.8 ?
C15 C16 C11 121.4(4) ?
C15 C16 H16 119.3 ?
C11 C16 H16 119.3 ?
C6 C17 H17a 109.5 ?
C6 C17 H17B 109.5 ?
H17a C17 H17B 109.5 ?
C6 C17 H17C 109.5 ?
H17a C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C6 C18 H18a 109.5 ?
C6 C18 H18B 109.5 ?
H18a C18 H18B 109.5 ?
C6 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
Br1 C12 . 1.910(5) ?
O2 C5 . 1.225(5) ?
O9 C10 . 1.357(6) yes
O9 C9 . 1.451(6) yes
O10 C10 . 1.231(6) yes
N1 C2 . 1.365(6) yes
N1 C8a . 1.381(6) yes
N1 H1 . .88 ?
C2 C3 . 1.347(6) yes
C2 C9 . 1.483(7) yes
C3 C4 . 1.510(7) yes
C3 C10 . 1.439(7) yes
C4 C4a . 1.533(6) yes
C4 C11 . 1.541(6) ?
C4 H4 . 1.00 ?
C4a C8a . 1.366(6) yes
C4a C5 . 1.463(7) yes
C5 C6 . 1.537(7) yes
C6 C7 . 1.533(7) yes
C6 C18 . 1.533(7) ?
C6 C17 . 1.544(7) ?
C7 C8 . 1.519(7) yes
C7 H7a . .99 ?
C7 H7B . .99 ?
C8 C8a . 1.493(7) yes
C8 H8a . .99 ?
C8 H8B . .99 ?
C9 H9a . .99 ?
C9 H9B . .99 ?
C11 C12 . 1.383(6) ?
C11 C16 . 1.402(6) ?
C12 C13 . 1.386(7) ?
C13 C14 . 1.389(7) ?
C13 H13 . .95 ?
C14 C15 . 1.391(7) ?
C14 H14 . .95 ?
C15 C16 . 1.381(7) ?
C15 H15 . .95 ?
C16 H16 . .95 ?
C17 H17a . .98 ?
C17 H17B . .98 ?
C17 H17C . .98 ?
C18 H18a . .98 ?
C18 H18B . .98 ?
C18 H18C . .98 ?
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
N1 H1 O10 2_544 .88 2.07 2.864(5) 149 yes
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
C8a N1 C2 C3 6.2(7) yes
C8a N1 C2 C9 -172.1(4) ?
N1 C2 C3 C10 175.8(4) ?
C9 C2 C3 C10 -5.6(5) ?
N1 C2 C3 C4 .8(7) yes
C9 C2 C3 C4 179.3(4) ?
C2 C3 C4 C4a -7.1(6) yes
C10 C3 C4 C4a 179.2(4) ?
C2 C3 C4 C11 115.5(5) ?
C10 C3 C4 C11 -58.2(6) ?
C3 C4 C4a C8a 7.6(6) yes
C11 C4 C4a C8a -114.1(5) ?
C3 C4 C4a C5 -172.4(4) ?
C11 C4 C4a C5 65.9(5) ?
C8a C4a C5 O2 -177.4(4) ?
C4 C4a C5 O2 2.6(7) ?
C8a C4a C5 C6 5.4(7) ?
C4 C4a C5 C6 -174.6(4) ?
O2 C5 C6 C7 153.6(4) ?
O2 C5 C6 C18 33.5(7) ?
C4a C5 C6 C18 -149.3(5) ?
O2 C5 C6 C17 -85.4(6) ?
C4a C5 C6 C17 91.8(5) ?
C18 C6 C7 C8 171.5(4) ?
C5 C6 C7 C8 50.6(6) ?
C17 C6 C7 C8 -67.9(6) ?
C6 C7 C8 C8a -48.0(6) ?
C5 C4a C8a N1 178.1(4) ?
C4 C4a C8a N1 -1.8(7) yes
C5 C4a C8a C8 -2.1(7) ?
C4 C4a C8a C8 177.9(4) ?
C4a C8a N1 C2 -5.5(7) yes
C2 N1 C8a C8 174.7(4) ?
C4a C5 C6 C7 -29.2(6) yes
C4a C8a C8 C7 23.5(7) yes
C7 C8 C8a N1 -156.8(4) ?
C10 O9 C9 C2 -5.0(5) ?
C3 C2 C9 O9 6.7(5) ?
N1 C2 C9 O9 -174.8(4) ?
C9 O9 C10 O10 179.8(4) ?
C9 O9 C10 C3 2.0(5) ?
C2 C3 C10 O10 -175.2(5) ?
C4 C3 C10 O10 -.5(8) ?
C2 C3 C10 O9 2.3(5) ?
C4 C3 C10 O9 176.9(4) ?
C3 C4 C11 C12 114.8(5) ?
C4a C4 C11 C12 -124.7(5) ?
C3 C4 C11 C16 -62.1(5) ?
C4a C4 C11 C16 58.3(5) ?
C16 C11 C12 C13 -.4(7) ?
C4 C11 C12 C13 -177.4(4) ?
C16 C11 C12 Br1 177.4(3) ?
C4 C11 C12 Br1 .5(6) ?
C11 C12 C13 C14 .1(8) ?
Br1 C12 C13 C14 -177.9(4) ?
C12 C13 C14 C15 .9(8) ?
C13 C14 C15 C16 -1.5(8) ?
C14 C15 C16 C11 1.1(8) ?
C12 C11 C16 C15 -.2(7) ?
C4 C11 C16 C15 177.0(4) ?
