#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/44/2204423.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_2204423
loop_
_publ_author_name
'Glagovich, Neil M.'
'Reed, Elizabeth M.'
'Crundwell, Guy'
'Updegraff, James B. III'
'Zeller, Matthias'
'Hunter, Allen D.'
_publ_section_title
;
 N-(9H-Fluoren-9-ylidene)-N-(-2-methoxyphenyl)amine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2000
_journal_page_last               o2001
_journal_paper_doi               10.1107/S1600536804024018
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H15 N O'
_chemical_formula_moiety         'C20 H15 N O'
_chemical_formula_sum            'C20 H15 N O'
_chemical_formula_weight         285.33
_chemical_melting_point          407
_chemical_name_systematic
;
N-(9H-fluoren-9-ylidene)-N-(-2-methoxyphenyl)amine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 116.8320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0517(5)
_cell_length_b                   9.3304(4)
_cell_length_c                   15.6876(9)
_cell_measurement_reflns_used    12300
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7
_cell_measurement_theta_min      2.18
_cell_volume                     1443.49(12)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997-1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1997-1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12925
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0802P)²+0.4989P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                3381
_reflns_number_total             3578
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6121.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'NO' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (40
times).

'_geom_angle_publ_flag' value 'NO' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (65
times).

'_geom_torsion_publ_flag' value 'NO' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (51 time).

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

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'NO' changed to 'no' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (40
times).

'_geom_angle_publ_flag' value 'NO' changed to 'no' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (65
times).

'_geom_torsion_publ_flag' value 'NO' changed to 'no'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (51
time).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204423
_cod_database_fobs_code          2204423
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_type_symbol
O1 0.84155(10) 0.21629(10) 0.19758(7) 0.0293(2) Uani d . 1 O
N1 0.89284(11) 0.41806(11) 0.09280(8) 0.0232(2) Uani d . 1 N
C1 0.68909(13) 0.19529(13) -0.07085(9) 0.0225(3) Uani d . 1 C
H1A 0.7697 0.1428 -0.0340 0.027 Uiso calc R 1 H
C2 0.57988(14) 0.13121(14) -0.14745(9) 0.0257(3) Uani d . 1 C
H2A 0.5868 0.0343 -0.1634 0.031 Uiso calc R 1 H
C3 0.46097(14) 0.20717(15) -0.20084(9) 0.0272(3) Uani d . 1 C
H3A 0.3878 0.1615 -0.2526 0.033 Uiso calc R 1 H
C4 0.44796(13) 0.34949(15) -0.17924(9) 0.0257(3) Uani d . 1 C
H4A 0.3663 0.4008 -0.2152 0.031 Uiso calc R 1 H
C5 0.48311(14) 0.67726(14) -0.09553(10) 0.0268(3) Uani d . 1 C
H5A 0.3939 0.6679 -0.1460 0.032 Uiso calc R 1 H
C6 0.52862(15) 0.80676(14) -0.04736(11) 0.0303(3) Uani d . 1 C
H6A 0.4694 0.8871 -0.0658 0.036 Uiso calc R 1 H
C7 0.65843(16) 0.82111(14) 0.02695(11) 0.0302(3) Uani d . 1 C
H7A 0.6870 0.9112 0.0578 0.036 Uiso calc R 1 H
C8 0.74776(14) 0.70452(14) 0.05697(10) 0.0262(3) Uani d . 1 C
H8A 0.8361 0.7131 0.1087 0.031 Uiso calc R 1 H
C9 0.77374(12) 0.43601(12) 0.02524(8) 0.0197(2) Uani d . 1 C
C10 0.67717(12) 0.33749(13) -0.04984(8) 0.0199(2) Uani d . 1 C
C11 0.55665(12) 0.41459(13) -0.10429(9) 0.0215(3) Uani d . 1 C
C12 0.57253(13) 0.56218(13) -0.06729(9) 0.0222(3) Uani d . 1 C
C13 0.70251(13) 0.57638(12) 0.00852(9) 0.0218(3) Uani d . 1 C
C14 0.95705(12) 0.28210(13) 0.10895(9) 0.0218(3) Uani d . 1 C
C15 0.93461(12) 0.17910(13) 0.16577(9) 0.0224(3) Uani d . 1 C
C16 1.00403(13) 0.04971(14) 0.18537(9) 0.0248(3) Uani d . 1 C
H16A 0.9889 -0.0203 0.2235 0.030 Uiso calc R 1 H
C17 1.09583(13) 0.02271(14) 0.14901(9) 0.0271(3) Uani d . 1 C
H17A 1.1423 -0.0664 0.1619 0.033 Uiso calc R 1 H
C18 1.11985(14) 0.12432(15) 0.09440(10) 0.0289(3) Uani d . 1 C
H18A 1.1828 0.1052 0.0700 0.035 Uiso calc R 1 H
C19 1.05154(13) 0.25466(14) 0.07532(9) 0.0259(3) Uani d . 1 C
H19A 1.0696 0.3254 0.0390 0.031 Uiso calc R 1 H
C20 0.81970(14) 0.11575(15) 0.25791(10) 0.0302(3) Uani d . 1 C
H20A 0.7531 0.1546 0.2769 0.045 Uiso calc R 1 H
H20B 0.9054 0.0980 0.3150 0.045 Uiso calc R 1 H
H20C 0.7856 0.0256 0.2232 0.045 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 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
_geom_angle_publ_flag
C15 O1 C20 116.91(10) no
C9 N1 C14 120.75(11) no
C10 C1 C2 118.43(12) no
C10 C1 H1A 120.8 no
C2 C1 H1A 120.8 no
C3 C2 C1 120.96(12) no
C3 C2 H2A 119.5 no
C1 C2 H2A 119.5 no
C2 C3 C4 120.79(12) no
C2 C3 H3A 119.6 no
C4 C3 H3A 119.6 no
C11 C4 C3 118.62(12) no
C11 C4 H4A 120.7 no
C3 C4 H4A 120.7 no
C12 C5 C6 117.81(13) no
C12 C5 H5A 121.1 no
C6 C5 H5A 121.1 no
C7 C6 C5 121.51(12) no
C7 C6 H6A 119.2 no
C5 C6 H6A 119.2 no
C6 C7 C8 120.82(13) no
C6 C7 H7A 119.6 no
C8 C7 H7A 119.6 no
C13 C8 C7 117.48(13) no
C13 C8 H8A 121.3 no
C7 C8 H8A 121.3 no
N1 C9 C13 121.83(11) no
N1 C9 C10 132.55(11) no
C13 C9 C10 105.62(10) no
C1 C10 C11 120.54(12) no
C1 C10 C9 131.63(11) no
C11 C10 C9 107.84(10) no
C4 C11 C10 120.65(12) no
C4 C11 C12 130.35(12) no
C10 C11 C12 109.00(11) no
C5 C12 C13 120.53(12) no
C5 C12 C11 130.94(12) no
C13 C12 C11 108.52(10) no
C8 C13 C12 121.82(11) no
C8 C13 C9 129.20(12) no
C12 C13 C9 108.97(10) no
C19 C14 C15 119.49(11) no
C19 C14 N1 119.84(11) no
C15 C14 N1 120.44(11) no
O1 C15 C16 124.62(11) no
O1 C15 C14 115.61(11) no
C16 C15 C14 119.76(11) no
C15 C16 C17 119.89(12) no
C15 C16 H16A 120.1 no
C17 C16 H16A 120.1 no
C18 C17 C16 120.61(12) no
C18 C17 H17A 119.7 no
C16 C17 H17A 119.7 no
C17 C18 C19 119.73(12) no
C17 C18 H18A 120.1 no
C19 C18 H18A 120.1 no
C14 C19 C18 120.48(12) no
C14 C19 H19A 119.8 no
C18 C19 H19A 119.8 no
O1 C20 H20A 109.5 no
O1 C20 H20B 109.5 no
H20A C20 H20B 109.5 no
O1 C20 H20C 109.5 no
H20A C20 H20C 109.5 no
H20B C20 H20C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 1.3750(15) no
O1 C20 1.4284(16) no
N1 C9 1.2746(16) no
N1 C14 1.4194(15) no
C1 C10 1.3877(16) no
C1 C2 1.3960(18) no
C1 H1A 0.9500 no
C2 C3 1.3919(19) no
C2 H2A 0.9500 no
C3 C4 1.3938(19) no
C3 H3A 0.9500 no
C4 C11 1.3854(18) no
C4 H4A 0.9500 no
C5 C12 1.3895(17) no
C5 C6 1.393(2) no
C5 H5A 0.9500 no
C6 C7 1.388(2) no
C6 H6A 0.9500 no
C7 C8 1.4000(18) no
C7 H7A 0.9500 no
C8 C13 1.3835(18) no
C8 H8A 0.9500 no
C9 C13 1.4891(15) no
C9 C10 1.4955(17) no
C10 C11 1.4122(16) no
C11 C12 1.4738(17) no
C12 C13 1.3976(18) no
C14 C19 1.3898(18) no
C14 C15 1.4069(17) no
C15 C16 1.3885(17) no
C16 C17 1.3929(18) no
C16 H16A 0.9500 no
C17 C18 1.3815(19) no
C17 H17A 0.9500 no
C18 C19 1.3909(18) no
C18 H18A 0.9500 no
C19 H19A 0.9500 no
C20 H20A 0.9800 no
C20 H20B 0.9800 no
C20 H20C 0.9800 no
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
C10 C1 C2 C3 -0.88(19) no
C1 C2 C3 C4 0.1(2) no
C2 C3 C4 C11 0.92(19) no
C12 C5 C6 C7 -0.50(19) no
C5 C6 C7 C8 -0.9(2) no
C6 C7 C8 C13 1.31(19) no
C14 N1 C9 C13 178.18(11) no
C14 N1 C9 C10 -1.6(2) no
C2 C1 C10 C11 0.63(18) no
C2 C1 C10 C9 -179.36(12) no
N1 C9 C10 C1 -2.0(2) no
C13 C9 C10 C1 178.26(12) no
N1 C9 C10 C11 178.04(13) no
C13 C9 C10 C11 -1.73(13) no
C3 C4 C11 C10 -1.16(18) no
C3 C4 C11 C12 178.52(12) no
C1 C10 C11 C4 0.39(18) no
C9 C10 C11 C4 -179.62(11) no
C1 C10 C11 C12 -179.36(10) no
C9 C10 C11 C12 0.64(13) no
C6 C5 C12 C13 1.46(18) no
C6 C5 C12 C11 -178.70(12) no
C4 C11 C12 C5 1.2(2) no
C10 C11 C12 C5 -179.06(12) no
C4 C11 C12 C13 -178.92(12) no
C10 C11 C12 C13 0.79(13) no
C7 C8 C13 C12 -0.34(18) no
C7 C8 C13 C9 -179.16(12) no
C5 C12 C13 C8 -1.06(18) no
C11 C12 C13 C8 179.06(11) no
C5 C12 C13 C9 177.97(11) no
C11 C12 C13 C9 -1.90(13) no
N1 C9 C13 C8 1.4(2) no
C10 C9 C13 C8 -178.81(12) no
N1 C9 C13 C12 -177.56(11) no
C10 C9 C13 C12 2.25(13) no
C9 N1 C14 C19 99.66(15) no
C9 N1 C14 C15 -85.84(15) no
C20 O1 C15 C16 2.46(19) no
C20 O1 C15 C14 -178.10(11) no
C19 C14 C15 O1 178.69(11) no
N1 C14 C15 O1 4.17(17) no
C19 C14 C15 C16 -1.83(18) no
N1 C14 C15 C16 -176.36(11) no
O1 C15 C16 C17 179.65(12) no
C14 C15 C16 C17 0.23(19) no
C15 C16 C17 C18 0.8(2) no
C16 C17 C18 C19 -0.2(2) no
C15 C14 C19 C18 2.46(19) no
N1 C14 C19 C18 177.02(12) no
C17 C18 C19 C14 -1.5(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130371
