#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/79/2237923.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_2237923
loop_
_publ_author_name
'Fan, Cui-Ping'
'Yin, Wei-Ping'
'Cao, Xin-Xiang'
'Yao, Jing-Cai'
_publ_section_title
;
 2-Bromo-1,6,6-trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione
;
_journal_coeditor_code           KP2449
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o834
_journal_paper_doi               10.1107/S1600536813011483
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C19 H17 Br O3'
_chemical_formula_moiety         'C19 H17 Br O3'
_chemical_formula_sum            'C19 H17 Br O3'
_chemical_formula_weight         373.24
_chemical_name_systematic
2-Bromo-1,6,6-trimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 96.7230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6063(12)
_cell_length_b                   7.0457(9)
_cell_length_c                   11.9688(15)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.95
_cell_measurement_theta_min      2.58
_cell_volume                     804.52(18)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6178
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    2.567
_exptl_absorpt_correction_T_max  0.7481
_exptl_absorpt_correction_T_min  0.3721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.412
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0329
_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)+(0.0469P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                1177
_reflns_number_total             1634
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kp2449.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2237923
_cod_database_fobs_code          2237923
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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
Br Br1 0.50666(4) 0.7500 -0.40805(3) 0.0774(2) Uani d S 1 2
C C1 0.9138(3) 0.7500 0.2002(2) 0.0392(7) Uani d S 1 2
C C2 0.7711(3) 0.7500 0.2173(2) 0.0365(7) Uani d S 1 2
C C3 0.6680(3) 0.7500 0.1229(2) 0.0354(7) Uani d S 1 2
C C4 0.7082(3) 0.7500 0.0134(2) 0.0371(7) Uani d S 1 2
C C5 0.8494(3) 0.7500 -0.0014(3) 0.0462(8) Uani d S 1 2
H H5 0.8766 0.7500 -0.0734 0.055 Uiso calc SR 1 2
C C6 0.9483(3) 0.7500 0.0909(3) 0.0471(8) Uani d S 1 2
H H6 1.0425 0.7500 0.0798 0.057 Uiso calc SR 1 2
C C7 0.5146(3) 0.7500 0.1357(3) 0.0456(8) Uani d S 1 2
C C8 0.4040(3) 0.7500 0.0286(3) 0.0440(8) Uani d S 1 2
C C9 0.4585(3) 0.7500 -0.0783(3) 0.0405(8) Uani d S 1 2
C C10 0.5998(3) 0.7500 -0.0809(3) 0.0387(7) Uani d S 1 2
C C11 0.3933(3) 0.7500 -0.1926(3) 0.0435(8) Uani d S 1 2
C C12 0.5002(4) 0.7500 -0.2540(3) 0.0490(8) Uani d S 1 2
C C13 0.2392(4) 0.7500 -0.2319(3) 0.0590(10) Uani d S 1 2
H H13A 0.2017 0.8744 -0.2222 0.088 Uiso calc PR 0.50 1
H H13B 0.1930 0.6601 -0.1886 0.088 Uiso calc PR 0.50 1
H H13C 0.2244 0.7155 -0.3100 0.088 Uiso calc PR 0.50 1
C C14 0.7287(4) 0.7500 0.3362(3) 0.0513(9) Uani d S 1 2
H H14A 0.7133 0.6252 0.3353 0.062 Uiso d PR 0.50 1
H H14B 0.6436 0.8237 0.3530 0.062 Uiso d PR 0.50 1
C C15 0.8496(5) 0.8191(7) 0.4235(4) 0.0587(15) Uani d P 0.50 1
H H15B 0.8751 0.9509 0.4144 0.070 Uiso d PR 0.50 1
H H15A 0.8219 0.8036 0.4983 0.070 Uiso d PR 0.50 1
C C16 0.9772(5) 0.7020(8) 0.4095(3) 0.058(2) Uani d P 0.50 1
H H16A 0.9494 0.5696 0.4079 0.070 Uiso d PR 0.50 1
H H16B 1.0497 0.7207 0.4721 0.070 Uiso d PR 0.50 1
C C17 1.0334(3) 0.7500 0.2971(3) 0.0495(8) Uani d S 1 2
C C18 1.1253(3) 0.5741(4) 0.2885(2) 0.0726(8) Uani d . 1 1
H H18A 1.1998 0.5740 0.3494 0.109 Uiso calc R 1 1
H H18B 1.1641 0.5760 0.2182 0.109 Uiso calc R 1 1
H H18C 1.0694 0.4619 0.2925 0.109 Uiso calc R 1 1
O O1 0.4673(3) 0.7500 0.2239(2) 0.0881(10) Uani d S 1 2
O O2 0.2812(3) 0.7500 0.0408(2) 0.0763(8) Uani d S 1 2
O O3 0.6299(2) 0.7500 -0.18897(17) 0.0468(6) Uani d S 1 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C6 C1 C2 . . 118.7(3)
C6 C1 C17 . . 118.2(3)
C2 C1 C17 . . 123.1(3)
C1 C2 C3 . . 119.2(3)
C1 C2 C14 . . 120.3(3)
C3 C2 C14 . . 120.5(3)
C4 C3 C2 . . 120.0(3)
C4 C3 C7 . . 118.4(3)
C2 C3 C7 . . 121.6(3)
C5 C4 C3 . . 119.8(3)
C5 C4 C10 . . 121.8(3)
C3 C4 C10 . . 118.4(3)
C6 C5 C4 . . 119.5(3)
C6 C5 H5 . . 120.2
C4 C5 H5 . . 120.2
C5 C6 C1 . . 122.7(3)
C5 C6 H6 . . 118.6
C1 C6 H6 . . 118.6
O1 C7 C3 . . 124.7(3)
O1 C7 C8 . . 115.5(3)
C3 C7 C8 . . 119.8(3)
O2 C8 C9 . . 124.8(3)
O2 C8 C7 . . 118.7(3)
C9 C8 C7 . . 116.4(3)
C10 C9 C11 . . 107.7(3)
C10 C9 C8 . . 119.2(3)
C11 C9 C8 . . 133.1(3)
O3 C10 C9 . . 110.2(3)
O3 C10 C4 . . 122.0(3)
C9 C10 C4 . . 127.8(3)
C12 C11 C9 . . 104.3(3)
C12 C11 C13 . . 128.6(3)
C9 C11 C13 . . 127.1(3)
C11 C12 O3 . . 112.9(3)
C11 C12 Br1 . . 131.9(3)
O3 C12 Br1 . . 115.2(2)
C11 C13 H13A . . 109.5
C11 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C11 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C2 C14 C15 . 4_575 111.7(3)
C2 C14 C15 . . 111.7(3)
C15 C14 C15 4_575 . 36.7(4)
C2 C14 H14A . . 92.9
C15 C14 H14A 4_575 . 79.0
C15 C14 H14A . . 115.4
C2 C14 H14B . . 119.8
C15 C14 H14B 4_575 . 126.1
C15 C14 H14B . . 105.4
H14A C14 H14B . . 111.9
C15 C15 C16 4_575 4_575 83.3(3)
C15 C15 C16 4_575 . 56.7(3)
C16 C15 C16 4_575 . 26.6(5)
C15 C15 C14 4_575 . 71.66(18)
C16 C15 C14 4_575 . 122.4(4)
C16 C15 C14 . . 108.0(3)
C15 C15 H15B 4_575 . 163.3
C16 C15 H15B 4_575 . 80.6
C16 C15 H15B . . 107.0
C14 C15 H15B . . 113.9
C15 C15 H15A 4_575 . 83.5
C16 C15 H15A 4_575 . 118.9
C16 C15 H15A . . 110.9
C14 C15 H15A . . 108.8
H15B C15 H15A . . 108.2
C16 C16 C15 4_575 4_575 96.7(3)
C16 C16 C15 4_575 . 56.7(3)
C15 C16 C15 4_575 . 40.0(4)
C16 C16 C17 4_575 . 77.4(2)
C15 C16 C17 4_575 . 125.7(4)
C15 C16 C17 . . 110.5(4)
C16 C16 H16A 4_575 . 164.1
C15 C16 H16A 4_575 . 67.7
C15 C16 H16A . . 107.7
C17 C16 H16A . . 108.5
C16 C16 H16B 4_575 . 82.2
C15 C16 H16B 4_575 . 122.2
C15 C16 H16B . . 111.1
C17 C16 H16B . . 110.5
H16A C16 H16B . . 108.5
C18 C17 C18 4_575 . 108.0(3)
C18 C17 C1 4_575 . 109.60(18)
C18 C17 C1 . . 109.60(18)
C18 C17 C16 4_575 4_575 98.3(3)
C18 C17 C16 . 4_575 119.9(3)
C1 C17 C16 . 4_575 110.6(3)
C18 C17 C16 4_575 . 119.9(3)
C18 C17 C16 . . 98.3(3)
C1 C17 C16 . . 110.6(3)
C16 C17 C16 4_575 . 25.3(4)
C17 C18 H18A . . 109.5
C17 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C17 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
C10 O3 C12 . . 104.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C12 . 1.852(3)
C1 C6 . 1.386(4)
C1 C2 . 1.410(4)
C1 C17 . 1.534(4)
C2 C3 . 1.412(4)
C2 C14 . 1.526(4)
C3 C4 . 1.409(4)
C3 C7 . 1.499(4)
C4 C5 . 1.388(4)
C4 C10 . 1.444(4)
C5 C6 . 1.371(4)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 O1 . 1.197(4)
C7 C8 . 1.566(5)
C8 O2 . 1.205(4)
C8 C9 . 1.439(4)
C9 C10 . 1.361(4)
C9 C11 . 1.436(4)
C10 O3 . 1.358(3)
C11 C12 . 1.331(5)
C11 C13 . 1.499(4)
C12 O3 . 1.389(4)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C14 C15 4_575 1.547(5)
C14 C15 . 1.547(5)
C14 H14A . 0.8918
C14 H14B . 1.0084
C15 C15 4_575 0.973(9)
C15 C16 4_575 1.265(6)
C15 C16 . 1.503(6)
C15 H15B . 0.9700
C15 H15A . 0.9700
C16 C16 4_575 0.677(12)
C16 C15 4_575 1.265(6)
C16 C17 . 1.545(5)
C16 H16A . 0.9700
C16 H16B . 0.9700
C17 C18 4_575 1.532(3)
C17 C18 . 1.532(3)
C17 C16 4_575 1.545(5)
C18 H18A . 0.9600
C18 H18B . 0.9600
C18 H18C . 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
C6 H6 O2 1_655 0.93 2.39 3.322(4) 177.0
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_4
_geom_torsion
C6 C1 C2 C3 . . 0.0
C17 C1 C2 C3 . . 180.0
C6 C1 C2 C14 . . 180.0
C17 C1 C2 C14 . . 0.0
C1 C2 C3 C4 . . 0.0
C14 C2 C3 C4 . . 180.0
C1 C2 C3 C7 . . 180.0
C14 C2 C3 C7 . . 0.0
C2 C3 C4 C5 . . 0.0000(10)
C7 C3 C4 C5 . . 180.0
C2 C3 C4 C10 . . 180.0
C7 C3 C4 C10 . . 0.0
C3 C4 C5 C6 . . 0.0000(10)
C10 C4 C5 C6 . . 180.0
C4 C5 C6 C1 . . 0.0
C2 C1 C6 C5 . . 0.0
C17 C1 C6 C5 . . 180.0
C4 C3 C7 O1 . . 180.0
C2 C3 C7 O1 . . 0.0
C4 C3 C7 C8 . . 0.0
C2 C3 C7 C8 . . 180.0
O1 C7 C8 O2 . . 0.0
C3 C7 C8 O2 . . 180.0
O1 C7 C8 C9 . . 180.0
C3 C7 C8 C9 . . 0.0
O2 C8 C9 C10 . . 180.0
C7 C8 C9 C10 . . 0.0
O2 C8 C9 C11 . . 0.0
C7 C8 C9 C11 . . 180.0
C11 C9 C10 O3 . . 0.0
C8 C9 C10 O3 . . 180.0
C11 C9 C10 C4 . . 180.0
C8 C9 C10 C4 . . 0.0
C5 C4 C10 O3 . . 0.0
C3 C4 C10 O3 . . 180.0
C5 C4 C10 C9 . . 180.0
C3 C4 C10 C9 . . 0.0
C10 C9 C11 C12 . . 0.0
C8 C9 C11 C12 . . 180.0
C10 C9 C11 C13 . . 180.0
C8 C9 C11 C13 . . 0.0
C9 C11 C12 O3 . . 0.0
C13 C11 C12 O3 . . 180.0
C9 C11 C12 Br1 . . 180.0
C13 C11 C12 Br1 . . 0.0
C1 C2 C14 C15 . 4_575 -19.8(2)
C3 C2 C14 C15 . 4_575 160.2(2)
C1 C2 C14 C15 . . 19.8(2)
C3 C2 C14 C15 . . -160.2(2)
C2 C14 C15 C15 . 4_575 -97.56(14)
C2 C14 C15 C16 . 4_575 -28.5(5)
C15 C14 C15 C16 4_575 4_575 69.1(5)
C2 C14 C15 C16 . . -53.3(4)
C15 C14 C15 C16 4_575 . 44.3(3)
C15 C15 C16 C16 4_575 4_575 180.000(2)
C14 C15 C16 C16 . 4_575 127.6(4)
C16 C15 C16 C15 4_575 4_575 180.0000(10)
C14 C15 C16 C15 . 4_575 -52.4(4)
C15 C15 C16 C17 4_575 . 121.6(4)
C16 C15 C16 C17 4_575 . -58.4(4)
C14 C15 C16 C17 . . 69.2(4)
C6 C1 C17 C18 . 4_575 59.21(19)
C2 C1 C17 C18 . 4_575 -120.79(19)
C6 C1 C17 C18 . . -59.21(19)
C2 C1 C17 C18 . . 120.79(19)
C6 C1 C17 C16 . 4_575 166.5(2)
C2 C1 C17 C16 . 4_575 -13.5(2)
C6 C1 C17 C16 . . -166.5(2)
C2 C1 C17 C16 . . 13.5(2)
C16 C16 C17 C18 4_575 4_575 34.1(2)
C15 C16 C17 C18 4_575 4_575 123.4(5)
C15 C16 C17 C18 . 4_575 81.0(4)
C16 C16 C17 C18 4_575 . 150.55(19)
C15 C16 C17 C18 4_575 . -120.2(6)
C15 C16 C17 C18 . . -162.6(3)
C16 C16 C17 C1 4_575 . -94.83(11)
C15 C16 C17 C1 4_575 . -5.6(6)
C15 C16 C17 C1 . . -48.0(4)
C15 C16 C17 C16 4_575 4_575 89.2(6)
C15 C16 C17 C16 . 4_575 46.8(4)
C9 C10 O3 C12 . . 0.0
C4 C10 O3 C12 . . 180.0
C11 C12 O3 C10 . . 0.0
Br1 C12 O3 C10 . . 180.0
