#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/28/2202821.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_2202821
loop_
_publ_author_name
'Shi, Daqing'
'Rong, Liangce'
'Wang, Juxian'
'Wang, Xiangshan'
'Hu, Hongwen'
_publ_section_title
3-Amino-1-(4-fluorophenyl)-3a,3b,6,7-tetrahydrobenz[4,5]indene-2-carbonitrile
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1562
_journal_page_last               o1563
_journal_paper_doi               10.1107/S1600536803020798
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C20 H17 F N2'
_chemical_formula_moiety         'C20 H17 F N2'
_chemical_formula_sum            'C20 H17 F N2'
_chemical_formula_weight         304.36
_chemical_melting_point          .472E-305
_chemical_name_systematic
3-Amino-1-(4-fluorophenyl)-3a,3b,6,7-tetrahydrobenzo[4,5]indene-2-carbonitrile
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.516(2)
_cell_length_b                   9.7100(10)
_cell_length_c                   14.914(2)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      14.37
_cell_measurement_theta_min      2.91
_cell_volume                     1618.4(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0090
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3487
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        2.92
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.089
_refine_ls_extinction_coef       0.0113(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.828
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0379
_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)+(0.0443P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                1534
_reflns_number_total             3005
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6305.cif
_cod_data_source_block           I
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2202821
_cod_database_fobs_code          2202821
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
F 0.55958(12) 0.56213(13) 0.10083(8) 0.1177(5) Uani d . 1 . . F
N1 0.32501(13) 0.17485(15) 0.55782(10) 0.0807(5) Uani d . 1 . . N
H1A 0.3819 0.1152 0.5665 0.097 Uiso calc R 1 . . H
H1B 0.2857 0.1874 0.5994 0.097 Uiso calc R 1 . . H
N2 0.50964(16) 0.0696(2) 0.39359(12) 0.1024(6) Uani d . 1 . . N
C1 0.31100(16) 0.41981(17) 0.17674(12) 0.0674(5) Uani d . 1 . . C
H1 0.2316 0.3956 0.1518 0.081 Uiso calc R 1 . . H
C2 0.3779(2) 0.47465(19) 0.11946(13) 0.0786(6) Uani d . 1 . . C
H2 0.3447 0.4861 0.0566 0.094 Uiso calc R 1 . . H
C3 0.4929(2) 0.51117(19) 0.15768(16) 0.0779(6) Uani d . 1 . . C
C4 0.54439(18) 0.4964(2) 0.24833(15) 0.0846(6) Uani d . 1 . . C
H4 0.6232 0.5235 0.2726 0.102 Uiso calc R 1 . . H
C5 0.47689(17) 0.4397(2) 0.30476(13) 0.0772(5) Uani d . 1 . . C
H5 0.5116 0.4281 0.3674 0.093 Uiso calc R 1 . . H
C6 0.35956(16) 0.40037(17) 0.26997(11) 0.0594(5) Uani d . 1 . . C
C7 0.28426(15) 0.33778(18) 0.32966(11) 0.0624(5) Uani d . 1 . . C
H7 0.2211 0.2836 0.2890 0.075 Uiso calc R 1 . . H
C8 0.34837(14) 0.24344(18) 0.40675(11) 0.0610(5) Uani d . 1 . . C
C9 0.29754(15) 0.24840(18) 0.47928(11) 0.0608(4) Uani d . 1 . . C
C10 0.19256(14) 0.34703(17) 0.45904(11) 0.0605(5) Uani d . 1 . . C
H10 0.1213 0.2935 0.4299 0.073 Uiso calc R 1 . . H
C11 0.22250(15) 0.43921(18) 0.38362(11) 0.0621(5) Uani d . 1 . . C
H11 0.1486 0.4747 0.3430 0.075 Uiso calc R 1 . . H
C12 0.30073(16) 0.55799(18) 0.42890(12) 0.0713(5) Uani d . 1 . . C
H12A 0.3197 0.6163 0.3816 0.086 Uiso calc R 1 . . H
H12B 0.3752 0.5222 0.4668 0.086 Uiso calc R 1 . . H
C13 0.23723(17) 0.64316(19) 0.48891(13) 0.0792(6) Uani d . 1 . . C
H13A 0.2928 0.7109 0.5228 0.095 Uiso calc R 1 . . H
H13B 0.1713 0.6925 0.4491 0.095 Uiso calc R 1 . . H
C14 0.18961(15) 0.5582(2) 0.55654(12) 0.0698(5) Uani d . 1 . . C
C15 0.16320(17) 0.6195(2) 0.63399(14) 0.0871(6) Uani d . 1 . . C
H15 0.1784 0.7128 0.6451 0.104 Uiso calc R 1 . . H
C16 0.11502(18) 0.5436(3) 0.69408(14) 0.0952(7) Uani d . 1 . . C
H16 0.0989 0.5858 0.7457 0.114 Uiso calc R 1 . . H
C17 0.09061(18) 0.4068(3) 0.67860(15) 0.0912(7) Uani d . 1 . . C
H17 0.0584 0.3556 0.7194 0.109 Uiso calc R 1 . . H
C18 0.11431(16) 0.3463(2) 0.60208(13) 0.0792(6) Uani d . 1 . . C
H18 0.0956 0.2538 0.5904 0.095 Uiso calc R 1 . . H
C19 0.16579(14) 0.41953(19) 0.54108(12) 0.0636(5) Uani d . 1 . . C
C20 0.43796(18) 0.1485(2) 0.39943(12) 0.0728(5) Uani d . 1 . . C
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'
F F 0.0171 0.0103 '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
C9 N1 H1A 120.0 ?
C9 N1 H1B 120.0 ?
H1A N1 H1B 120.0 ?
C6 C1 C2 121.51(18) ?
C6 C1 H1 119.2 ?
C2 C1 H1 119.2 ?
C3 C2 C1 118.19(18) ?
C3 C2 H2 120.9 ?
C1 C2 H2 120.9 ?
C4 C3 C2 122.89(18) ?
C4 C3 F 118.9(2) ?
C2 C3 F 118.2(2) ?
C3 C4 C5 118.34(19) ?
C3 C4 H4 120.8 ?
C5 C4 H4 120.8 ?
C6 C5 C4 121.49(18) ?
C6 C5 H5 119.3 ?
C4 C5 H5 119.3 ?
C5 C6 C1 117.56(16) ?
C5 C6 C7 122.61(16) ?
C1 C6 C7 119.83(16) ?
C6 C7 C8 116.50(10) yes
C6 C7 C11 116.79(14) ?
C8 C7 C11 101.00(10) yes
C6 C7 H7 107.3 ?
C8 C7 H7 107.3 ?
C11 C7 H7 107.3 ?
C9 C8 C20 123.62(15) ?
C9 C8 C7 111.10(10) yes
C20 C8 C7 124.70(10) yes
N1 C9 C8 128.6(2) yes
N1 C9 C10 121.30(10) yes
C8 C9 C10 110.00(10) yes
C19 C10 C9 116.33(14) ?
C19 C10 C11 116.57(14) ?
C9 C10 C11 101.80(10) yes
C19 C10 H10 107.2 ?
C9 C10 H10 107.2 ?
C11 C10 H10 107.2 ?
C12 C11 C10 109.27(14) ?
C12 C11 C7 114.62(13) ?
C10 C11 C7 102.80(10) yes
C12 C11 H11 110.0 ?
C10 C11 H11 110.0 ?
C7 C11 H11 110.0 ?
C11 C12 C13 110.80(14) ?
C11 C12 H12A 109.5 ?
C13 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
C13 C12 H12B 109.5 ?
H12A C12 H12B 108.1 ?
C14 C13 C12 113.53(15) ?
C14 C13 H13A 108.9 ?
C12 C13 H13A 108.9 ?
C14 C13 H13B 108.9 ?
C12 C13 H13B 108.9 ?
H13A C13 H13B 107.7 ?
C19 C14 C15 118.59(19) ?
C19 C14 C13 120.78(16) ?
C15 C14 C13 120.6(2) ?
C16 C15 C14 120.9(2) ?
C16 C15 H15 119.6 ?
C14 C15 H15 119.6 ?
C17 C16 C15 120.6(2) ?
C17 C16 H16 119.7 ?
C15 C16 H16 119.7 ?
C16 C17 C18 119.0(2) ?
C16 C17 H17 120.5 ?
C18 C17 H17 120.5 ?
C17 C18 C19 121.8(2) ?
C17 C18 H18 119.1 ?
C19 C18 H18 119.1 ?
C14 C19 C18 119.09(17) ?
C14 C19 C10 121.28(16) ?
C18 C19 C10 119.62(17) ?
N2 C20 C8 178.9(2) ?
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
F C3 . 1.367(2) yes
N1 C9 . 1.343(2) yes
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
N2 C20 . 1.145(2) yes
C1 C6 . 1.381(2) ?
C1 C2 . 1.387(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.356(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.346(3) ?
C4 C5 . 1.390(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.379(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.512(2) ?
C7 C8 . 1.515(2) yes
C7 C11 . 1.549(2) yes
C7 H7 . 0.9800 ?
C8 C9 . 1.349(2) yes
C8 C20 . 1.407(2) yes
C9 C10 . 1.514(2) yes
C10 C19 . 1.507(2) ?
C10 C11 . 1.540(2) yes
C10 H10 . 0.9800 ?
C11 C12 . 1.518(2) ?
C11 H11 . 0.9800 ?
C12 C13 . 1.528(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.505(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C19 . 1.383(2) ?
C14 C15 . 1.396(2) ?
C15 C16 . 1.376(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.365(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.369(2) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.395(2) ?
C18 H18 . 0.9300 ?
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
N1 H1A N2 3_656 0.86 2.19 3.019(2) 163
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
C6 C1 C2 C3 -1.0(3) ?
C1 C2 C3 C4 0.0(3) ?
C1 C2 C3 F 178.46(16) ?
C2 C3 C4 C5 0.8(3) ?
F C3 C4 C5 -177.64(16) ?
C3 C4 C5 C6 -0.7(3) ?
C4 C5 C6 C1 -0.3(3) ?
C4 C5 C6 C7 179.68(16) ?
C2 C1 C6 C5 1.1(3) ?
C2 C1 C6 C7 -178.85(16) ?
C5 C6 C7 C8 -35.8(2) yes
C1 C6 C7 C8 144.18(15) ?
C5 C6 C7 C11 83.6(2) yes
C1 C6 C7 C11 -96.44(19) ?
C6 C7 C8 C9 149.35(16) ?
C11 C7 C8 C9 21.76(19) ?
C6 C7 C8 C20 -39.0(2) ?
C11 C7 C8 C20 -166.62(17) ?
C20 C8 C9 N1 4.6(3) yes
C7 C8 C9 N1 176.29(17) yes
C20 C8 C9 C10 -171.6(2) ?
C7 C8 C9 C10 0.1(2) ?
N1 C9 C10 C19 33.5(2) yes
C8 C9 C10 C19 -150.00(16) ?
N1 C9 C10 C11 161.3(2) yes
C8 C9 C10 C11 -22.17(19) ?
C19 C10 C11 C12 39.85(19) ?
C9 C10 C11 C12 -87.82(15) ?
C19 C10 C11 C7 161.99(14) ?
C9 C10 C11 C7 34.32(16) ?
C6 C7 C11 C12 -42.9(2) yes
C8 C7 C11 C12 84.48(16) ?
C6 C7 C11 C10 -161.37(14) ?
C8 C7 C11 C10 -33.98(16) ?
C10 C11 C12 C13 -59.07(17) ?
C7 C11 C12 C13 -173.82(14) ?
C11 C12 C13 C14 51.5(2) ?
C12 C13 C14 C19 -23.0(2) ?
C12 C13 C14 C15 160.10(16) ?
C19 C14 C15 C16 0.3(3) ?
C13 C14 C15 C16 177.31(17) ?
C14 C15 C16 C17 -0.8(3) ?
C15 C16 C17 C18 -0.3(3) ?
C16 C17 C18 C19 1.9(3) ?
C15 C14 C19 C18 1.2(3) ?
C13 C14 C19 C18 -175.78(15) ?
C15 C14 C19 C10 -179.77(15) ?
C13 C14 C19 C10 3.2(3) ?
C17 C18 C19 C14 -2.3(3) ?
C17 C18 C19 C10 178.62(16) ?
C9 C10 C19 C14 107.93(19) ?
C11 C10 C19 C14 -12.2(2) ?
C9 C10 C19 C18 -73.1(2) ?
C11 C10 C19 C18 166.77(15) ?
