#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007034.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_2007034
loop_
_publ_author_name
'Chinnakali, K.'
'Fun, H.-K.'
'Sriraghavan, K.'
'Ramakrishnan, V. T.'
_publ_section_title
;
 8-(2-Bromo-4-methylanilino)-9-hydroxy-4-methyl-7,8,9,10-tetrahydro-7,8-benzocoumarin
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9800003
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C21 H20 Br N O3'
_chemical_formula_sum            'C21 H20 Br N O3'
_chemical_formula_weight         414.29
_chemical_name_systematic
;
8-(2-Bromo-4-methylanilino)-9-hydroxy-4-methyl-7,8,9,10-tetrahydro-7,8-
benzocoumarin
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.204(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.8970(18)
_cell_length_b                   11.878(2)
_cell_length_c                   8.0208(12)
_cell_measurement_reflns_used    43
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.573
_cell_measurement_theta_min      5.455
_cell_volume                     1880.6(5)
_computing_cell_refinement       'XSCANS (Siemens, 1994)'
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'XSCANS (Siemens, 1994)'
_computing_molecular_graphics    'SHELXTL-PC (Sheldrick, 1990)'
_computing_publication_material
; SHELXL-93 (Sheldrick, 1993)
  PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL-PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4 diffractometer'
_diffrn_measurement_method       '\q/2\q 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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            5654
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  0.432
_exptl_absorpt_correction_T_min  0.296
_exptl_absorpt_correction_type   'empirical \y scans (Siemens, 1994)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.501
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.833
_refine_ls_goodness_of_fit_obs   1.126
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.849
_refine_ls_restrained_S_obs      1.126
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_obs          0.0437
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1225
_refine_ls_wR_factor_obs         0.1026
_reflns_number_observed          1879
_reflns_number_total             4284
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    qa0031.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2007034
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br 0.0900(3) 0.0405(2) 0.1589(5) -0.0013(2) 0.0340(3) 0.0108(3)
O1 0.0446(11) 0.0376(11) 0.093(2) -0.0084(10) 0.0148(12) 0.0013(13)
C2 0.053(2) 0.049(2) 0.090(3) -0.012(2) 0.006(2) 0.002(2)
C3 0.063(2) 0.041(2) 0.109(4) -0.017(2) 0.013(2) 0.008(2)
C4 0.067(2) 0.034(2) 0.076(3) -0.005(2) -0.002(2) 0.001(2)
C5 0.057(2) 0.037(2) 0.107(3) 0.009(2) 0.013(2) -0.004(2)
C6 0.047(2) 0.045(2) 0.098(3) 0.003(2) 0.016(2) -0.007(2)
C7 0.044(2) 0.038(2) 0.065(2) 0.0012(14) 0.007(2) 0.000(2)
C8 0.041(2) 0.0362(15) 0.061(2) 0.0004(12) 0.003(2) -0.001(2)
C9 0.040(2) 0.041(2) 0.065(2) -0.0028(14) 0.005(2) 0.001(2)
C10 0.053(2) 0.037(2) 0.070(3) -0.0028(15) -0.002(2) 0.003(2)
O11 0.0538(14) 0.0572(15) 0.163(3) -0.0104(12) 0.040(2) 0.004(2)
C12 0.084(3) 0.031(2) 0.122(5) -0.003(2) 0.013(4) 0.002(3)
C13 0.047(2) 0.045(2) 0.078(3) -0.003(2) 0.017(2) -0.002(2)
C14 0.045(2) 0.037(2) 0.070(3) -0.0032(13) 0.014(2) 0.005(2)
C15 0.047(2) 0.035(2) 0.065(3) -0.0020(14) 0.010(2) -0.004(2)
C16 0.041(2) 0.0332(15) 0.077(3) -0.0012(14) 0.011(2) -0.001(2)
O17 0.0547(15) 0.0337(12) 0.117(2) 0.0019(11) 0.027(2) -0.0020(13)
N18 0.050(2) 0.0388(14) 0.072(2) -0.0085(13) 0.017(2) 0.001(2)
C19 0.047(2) 0.047(2) 0.055(2) -0.005(2) 0.019(2) -0.009(2)
C20 0.052(2) 0.054(2) 0.077(3) -0.014(2) 0.018(2) 0.003(2)
C21 0.053(2) 0.083(3) 0.073(3) -0.004(2) 0.008(2) 0.005(3)
C22 0.051(2) 0.095(3) 0.089(3) -0.021(2) 0.011(2) -0.012(3)
C23 0.067(3) 0.063(2) 0.108(4) -0.026(2) 0.035(3) -0.018(3)
C24 0.056(2) 0.042(2) 0.087(3) -0.009(2) 0.025(2) -0.008(2)
C25 0.066(3) 0.147(5) 0.147(5) -0.043(3) 0.005(3) -0.029(4)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Br 0.16979(2) -0.03046(3) 0.49627(7) 0.0949(2) Uani d . 1 Br
O1 0.43772(10) 0.5801(2) 0.3165(3) 0.0578(6) Uani d . 1 O
C2 0.4790(2) 0.6676(3) 0.2841(5) 0.0639(10) Uani d . 1 C
C3 0.4552(2) 0.7801(3) 0.3107(6) 0.0709(12) Uani d . 1 C
C4 0.3949(2) 0.8017(3) 0.3631(5) 0.0601(10) Uani d . 1 C
C5 0.2879(2) 0.7170(3) 0.4485(6) 0.0671(11) Uani d . 1 C
C6 0.2507(2) 0.6245(3) 0.4734(5) 0.0629(11) Uani d . 1 C
C7 0.27412(15) 0.5157(3) 0.4471(4) 0.0492(8) Uani d . 1 C
C8 0.33778(14) 0.5022(2) 0.3938(4) 0.0464(8) Uani d . 1 C
C9 0.37494(14) 0.5985(3) 0.3702(4) 0.0491(8) Uani d . 1 C
C10 0.3521(2) 0.7074(3) 0.3946(5) 0.0542(9) Uani d . 1 C
O11 0.53234(12) 0.6414(2) 0.2363(4) 0.0892(9) Uani d . 1 O
C12 0.3716(3) 0.9207(3) 0.3846(9) 0.0790(15) Uani d . 1 C
C13 0.2307(2) 0.4156(3) 0.4773(6) 0.0560(10) Uani d . 1 C
C14 0.2504(2) 0.3118(3) 0.3811(5) 0.0499(9) Uani d . 1 C
C15 0.3261(2) 0.2936(3) 0.4325(5) 0.0487(8) Uani d . 1 C
C16 0.3656(2) 0.3871(3) 0.3608(6) 0.0501(9) Uani d . 1 C
O17 0.34392(13) 0.1852(2) 0.3763(4) 0.0671(8) Uani d . 1 O
N18 0.21404(14) 0.2105(2) 0.4234(4) 0.0527(7) Uani d . 1 N
C19 0.1494(2) 0.1872(3) 0.3460(4) 0.0485(8) Uani d . 1 C
C20 0.1094(2) 0.2650(3) 0.2503(5) 0.0600(10) Uani d . 1 C
C21 0.0440(2) 0.2408(4) 0.1783(6) 0.0697(11) Uani d . 1 C
C22 0.0150(2) 0.1368(4) 0.1997(6) 0.0781(12) Uani d . 1 C
C23 0.0534(2) 0.0581(4) 0.2972(6) 0.0770(13) Uani d . 1 C
C24 0.1192(2) 0.0821(3) 0.3671(5) 0.0605(10) Uani d . 1 C
C25 -0.0573(2) 0.1112(5) 0.1225(7) 0.120(2) Uani d . 1 C
H25A -0.0653(7) 0.0316(6) 0.126(5) 0.181 Uiso calc R 1 H
H25B -0.0638(6) 0.136(3) 0.0078(17) 0.181 Uiso calc R 1 H
H25C -0.0886(2) 0.150(3) 0.185(3) 0.181 Uiso calc R 1 H
H3 0.487(2) 0.838(4) 0.295(5) 0.107(15) Uiso d . 1 H
H5 0.2701(16) 0.792(3) 0.464(4) 0.072(11) Uiso d . 1 H
H6 0.2117(16) 0.633(3) 0.520(4) 0.062(10) Uiso d . 1 H
H12A 0.324(3) 0.937(4) 0.295(6) 0.123(16) Uiso d . 1 H
H12B 0.402(2) 0.957(4) 0.361(6) 0.090(16) Uiso d . 1 H
H12C 0.359(2) 0.937(4) 0.491(6) 0.091(17) Uiso d . 1 H
H13A 0.2336(18) 0.406(3) 0.586(5) 0.073(14) Uiso d . 1 H
H13B 0.178(2) 0.439(4) 0.435(5) 0.109(14) Uiso d . 1 H
H14 0.2452(14) 0.324(3) 0.261(4) 0.049(9) Uiso d . 1 H
H15 0.3360(14) 0.297(3) 0.556(4) 0.051(10) Uiso d . 1 H
H16A 0.4123(17) 0.382(3) 0.411(4) 0.061(10) Uiso d . 1 H
H16B 0.3618(15) 0.375(3) 0.233(5) 0.062(11) Uiso d . 1 H
H17 0.382(2) 0.179(4) 0.363(6) 0.105(17) Uiso d . 1 H
H18 0.2394(15) 0.154(3) 0.436(4) 0.053(10) Uiso d . 1 H
H20 0.1279(15) 0.320(3) 0.222(4) 0.045(9) Uiso d . 1 H
H21 0.0247(16) 0.287(3) 0.089(4) 0.059(11) Uiso d . 1 H
H23 0.030(2) -0.005(4) 0.320(6) 0.100(14) Uiso d . 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 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'
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
_geom_angle_publ_flag
C2 O1 C9 121.6(3) ?
O11 C2 O1 115.7(3) yes
O11 C2 C3 126.9(3) yes
O1 C2 C3 117.3(3) ?
C4 C3 C2 123.0(3) ?
C3 C4 C10 118.4(3) ?
C3 C4 C12 121.0(4) ?
C10 C4 C12 120.6(4) ?
C6 C5 C10 121.0(3) ?
C5 C6 C7 121.9(3) ?
C8 C7 C6 119.0(3) ?
C8 C7 C13 121.2(3) ?
C6 C7 C13 119.7(3) ?
C9 C8 C7 117.8(3) ?
C9 C8 C16 120.6(3) ?
C7 C8 C16 121.6(3) ?
C8 C9 O1 115.3(3) yes
C8 C9 C10 123.9(3) ?
O1 C9 C10 120.8(3) ?
C9 C10 C5 116.4(3) ?
C9 C10 C4 118.9(3) ?
C5 C10 C4 124.7(3) yes
C7 C13 C14 111.5(3) ?
N18 C14 C15 108.7(3) ?
N18 C14 C13 112.3(3) ?
C15 C14 C13 106.5(3) ?
O17 C15 C16 112.4(3) ?
O17 C15 C14 108.6(3) ?
C16 C15 C14 109.5(3) ?
C8 C16 C15 112.2(3) ?
C19 N18 C14 121.2(3) ?
N18 C19 C20 123.5(3) ?
N18 C19 C24 120.8(3) ?
C20 C19 C24 115.7(3) ?
C19 C20 C21 122.4(4) ?
C22 C21 C20 121.2(4) ?
C21 C22 C23 117.6(4) ?
C21 C22 C25 120.9(5) ?
C23 C22 C25 121.4(4) ?
C22 C23 C24 121.0(4) ?
C23 C24 C19 122.0(4) ?
C23 C24 Br 119.0(3) ?
C19 C24 Br 119.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C24 1.901(4) ?
O1 C2 1.370(4) ?
O1 C9 1.389(3) ?
C2 O11 1.214(4) ?
C2 C3 1.442(5) ?
C3 C4 1.345(5) yes
C4 C10 1.448(4) ?
C4 C12 1.505(5) ?
C5 C6 1.354(5) yes
C5 C10 1.404(5) ?
C6 C7 1.399(4) ?
C7 C8 1.396(4) ?
C7 C13 1.506(5) ?
C8 C9 1.388(4) ?
C8 C16 1.510(4) ?
C9 C10 1.393(4) ?
C13 C14 1.531(5) ?
C14 N18 1.465(4) yes
C14 C15 1.526(4) ?
C15 O17 1.424(4) yes
C15 C16 1.515(4) ?
N18 C19 1.384(4) yes
C19 C20 1.386(5) ?
C19 C24 1.405(4) ?
C20 C21 1.387(5) ?
C21 C22 1.384(6) ?
C22 C23 1.385(6) ?
C22 C25 1.525(5) ?
C23 C24 1.387(5) ?
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
O17 H17 O11 2_645 0.77(4) 2.03(4) 2.776(4) 163(4) yes
N18 H18 Br 1_555 0.84(3) 2.67(3) 3.073(3) 111(2) yes
N18 H18 O17 1_555 0.84(3) 2.22(3) 2.675(4) 114(2) 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
C9 O1 C2 O11 -179.3(3) ?
C9 O1 C2 C3 1.0(5) ?
O11 C2 C3 C4 179.5(4) ?
O1 C2 C3 C4 -0.8(6) ?
C2 C3 C4 C10 0.2(6) ?
C2 C3 C4 C12 -178.4(5) ?
C10 C5 C6 C7 0.0(6) ?
C5 C6 C7 C8 0.1(6) ?
C5 C6 C7 C13 179.8(4) ?
C6 C7 C8 C9 0.3(5) ?
C13 C7 C8 C9 -179.4(4) ?
C6 C7 C8 C16 -179.1(4) ?
C13 C7 C8 C16 1.2(5) yes
C7 C8 C9 O1 -179.7(3) ?
C16 C8 C9 O1 -0.3(5) ?
C7 C8 C9 C10 -0.8(5) ?
C16 C8 C9 C10 178.6(4) ?
C2 O1 C9 C8 178.3(3) ?
C2 O1 C9 C10 -0.6(5) ?
C8 C9 C10 C5 0.9(5) ?
O1 C9 C10 C5 179.8(3) ?
C8 C9 C10 C4 -178.9(3) ?
O1 C9 C10 C4 0.0(5) ?
C6 C5 C10 C9 -0.5(6) ?
C6 C5 C10 C4 179.3(4) ?
C3 C4 C10 C9 0.2(5) ?
C12 C4 C10 C9 178.8(4) ?
C3 C4 C10 C5 -179.6(4) ?
C12 C4 C10 C5 -1.0(6) ?
C8 C7 C13 C14 -22.2(5) yes
C6 C7 C13 C14 158.0(4) ?
C7 C13 C14 N18 173.6(3) ?
C7 C13 C14 C15 54.8(4) yes
N18 C14 C15 O17 46.2(4) ?
C13 C14 C15 O17 167.4(3) ?
N18 C14 C15 C16 169.3(3) ?
C13 C14 C15 C16 -69.5(4) yes
C9 C8 C16 C15 166.3(3) ?
C7 C8 C16 C15 -14.4(5) yes
O17 C15 C16 C8 169.3(3) ?
C14 C15 C16 C8 48.5(4) yes
C15 C14 N18 C19 -159.1(3) ?
C13 C14 N18 C19 83.3(4) ?
C14 N18 C19 C20 -12.9(5) ?
C14 N18 C19 C24 169.9(3) ?
N18 C19 C20 C21 -178.0(3) ?
C24 C19 C20 C21 -0.6(5) ?
C19 C20 C21 C22 0.4(6) ?
C20 C21 C22 C23 0.8(6) ?
C20 C21 C22 C25 179.1(4) ?
C21 C22 C23 C24 -1.6(6) ?
C25 C22 C23 C24 -179.9(4) ?
C22 C23 C24 C19 1.4(6) ?
C22 C23 C24 Br -178.8(3) ?
N18 C19 C24 C23 177.1(3) ?
C20 C19 C24 C23 -0.3(5) ?
N18 C19 C24 Br -2.6(4) ?
C20 C19 C24 Br 180.0(3) ?