#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/39/2203915.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_2203915
loop_
_publ_author_name
'Glagovich, Neil M.'
'Reed, Elizabeth M.'
'Crundwell, Guy'
'Updegraff III, James B.'
'Zeller, Matthias'
'Hunter, Allen D.'
_publ_section_title
;
 N-9H-Fluoren-9-ylidene-3,4-dimethylaniline
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1269
_journal_page_last               o1270
_journal_paper_doi               10.1107/S1600536804015089
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C21 H17 N'
_chemical_formula_moiety         'C21 H17 N'
_chemical_formula_sum            'C21 H17 N'
_chemical_formula_weight         283.36
_chemical_melting_point          355.8
_chemical_name_systematic
;
N-9H-Fluoren-9-ylidene-3,4-dimethyaniline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                78.886(6)
_cell_angle_beta                 79.375(6)
_cell_angle_gamma                89.483(6)
_cell_formula_units_Z            2
_cell_length_a                   8.476(3)
_cell_length_b                   8.870(3)
_cell_length_c                   10.376(4)
_cell_measurement_reflns_used    6350
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.366
_cell_measurement_theta_min      2.342
_cell_volume                     752.1(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (1997-1999)'
_computing_data_reduction        'SAINT-Plus (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 0.994
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7401
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0543
_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)+(0.0842P)²+0.226P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                3472
_reflns_number_total             3722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6231.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 (42
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 (70
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:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 (42
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 (70
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_database_code               2203915
_cod_database_fobs_code          2203915
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 0.17433(12) 0.46338(11) 0.67607(10) 0.0192(2) Uani d . 1 N
C1 -0.04904(13) 0.25424(13) 0.90276(11) 0.0185(2) Uani d . 1 C
H1B 0.0335 0.1957 0.8625 0.022 Uiso calc R 1 H
C2 -0.16822(14) 0.18367(13) 1.00806(11) 0.0202(2) Uani d . 1 C
H2A -0.1672 0.0759 1.0399 0.024 Uiso calc R 1 H
C3 -0.28873(14) 0.27017(14) 1.06676(12) 0.0216(3) Uani d . 1 C
H3A -0.3690 0.2205 1.1385 0.026 Uiso calc R 1 H
C4 -0.29349(14) 0.42875(14) 1.02188(11) 0.0204(2) Uani d . 1 C
H4A -0.3757 0.4874 1.0623 0.024 Uiso calc R 1 H
C5 -0.23586(14) 0.78863(13) 0.86896(11) 0.0201(2) Uani d . 1 C
H5A -0.3286 0.7805 0.9374 0.024 Uiso calc R 1 H
C6 -0.18410(15) 0.93022(14) 0.78815(12) 0.0219(3) Uani d . 1 C
H6A -0.2426 1.0195 0.8015 0.026 Uiso calc R 1 H
C7 -0.04821(14) 0.94273(13) 0.68831(12) 0.0213(3) Uani d . 1 C
H7A -0.0147 1.0405 0.6348 0.026 Uiso calc R 1 H
C8 0.03990(14) 0.81344(13) 0.66552(11) 0.0190(2) Uani d . 1 C
H8A 0.1326 0.8222 0.5970 0.023 Uiso calc R 1 H
C9 0.05504(13) 0.51429(12) 0.74783(11) 0.0158(2) Uani d . 1 C
C10 -0.05363(13) 0.41135(13) 0.85820(11) 0.0161(2) Uani d . 1 C
C11 -0.17535(13) 0.49860(12) 0.91689(11) 0.0164(2) Uani d . 1 C
C12 -0.14870(13) 0.65976(13) 0.84713(11) 0.0168(2) Uani d . 1 C
C13 -0.01134(13) 0.67170(12) 0.74549(11) 0.0162(2) Uani d . 1 C
C14 0.27151(13) 0.56591(12) 0.56911(11) 0.0181(2) Uani d . 1 C
C15 0.40697(13) 0.63838(13) 0.59043(11) 0.0182(2) Uani d . 1 C
H15A 0.4322 0.6207 0.6775 0.022 Uiso calc R 1 H
C16 0.50606(13) 0.73612(13) 0.48654(11) 0.0183(2) Uani d . 1 C
C17 0.47049(13) 0.76004(13) 0.35730(11) 0.0188(2) Uani d . 1 C
C18 0.33727(14) 0.68383(14) 0.33679(12) 0.0205(2) Uani d . 1 C
H18A 0.3136 0.6982 0.2493 0.025 Uiso calc R 1 H
C19 0.23786(14) 0.58724(14) 0.44088(12) 0.0209(2) Uani d . 1 C
H19A 0.1476 0.5362 0.4245 0.025 Uiso calc R 1 H
C20 0.65200(15) 0.81173(15) 0.51315(13) 0.0260(3) Uani d . 1 C
H20A 0.6592 0.7798 0.6076 0.039 Uiso calc R 1 H
H20B 0.6432 0.9237 0.4917 0.039 Uiso calc R 1 H
H20C 0.7485 0.7810 0.4574 0.039 Uiso calc R 1 H
C21 0.57716(15) 0.86252(15) 0.24221(13) 0.0270(3) Uani d . 1 C
H21A 0.5281 0.8747 0.1625 0.040 Uiso calc R 1 H
H21B 0.6824 0.8162 0.2244 0.040 Uiso calc R 1 H
H21C 0.5904 0.9634 0.2648 0.040 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'
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 C14 119.74(10) no
C10 C1 C2 118.56(10) no
C10 C1 H1B 120.7 no
C2 C1 H1B 120.7 no
C3 C2 C1 120.44(11) no
C3 C2 H2A 119.8 no
C1 C2 H2A 119.8 no
C2 C3 C4 121.04(11) no
C2 C3 H3A 119.5 no
C4 C3 H3A 119.5 no
C11 C4 C3 118.44(11) no
C11 C4 H4A 120.8 no
C3 C4 H4A 120.8 no
C12 C5 C6 118.42(11) no
C12 C5 H5A 120.8 no
C6 C5 H5A 120.8 no
C7 C6 C5 120.97(11) no
C7 C6 H6A 119.5 no
C5 C6 H6A 119.5 no
C6 C7 C8 120.93(11) no
C6 C7 H7A 119.5 no
C8 C7 H7A 119.5 no
C13 C8 C7 118.41(11) no
C13 C8 H8A 120.8 no
C7 C8 H8A 120.8 no
N1 C9 C10 121.98(10) no
N1 C9 C13 132.58(10) no
C10 C9 C13 105.44(9) no
C1 C10 C11 121.07(10) no
C1 C10 C9 129.78(10) no
C11 C10 C9 109.14(10) no
C4 C11 C10 120.44(10) no
C4 C11 C12 131.40(10) no
C10 C11 C12 108.16(10) no
C5 C12 C13 120.82(11) no
C5 C12 C11 129.79(10) no
C13 C12 C11 109.39(10) no
C8 C13 C12 120.44(10) no
C8 C13 C9 131.69(10) no
C12 C13 C9 107.86(9) no
C19 C14 C15 119.39(11) no
C19 C14 N1 120.24(10) no
C15 C14 N1 120.24(10) no
C16 C15 C14 121.25(11) no
C16 C15 H15A 119.4 no
C14 C15 H15A 119.4 no
C15 C16 C17 119.39(11) no
C15 C16 C20 119.78(11) no
C17 C16 C20 120.81(11) no
C18 C17 C16 118.73(10) no
C18 C17 C21 120.55(11) no
C16 C17 C21 120.70(11) no
C19 C18 C17 121.75(11) no
C19 C18 H18A 119.1 no
C17 C18 H18A 119.1 no
C14 C19 C18 119.45(11) no
C14 C19 H19A 120.3 no
C18 C19 H19A 120.3 no
C16 C20 H20A 109.5 no
C16 C20 H20B 109.5 no
H20A C20 H20B 109.5 no
C16 C20 H20C 109.5 no
H20A C20 H20C 109.5 no
H20B C20 H20C 109.5 no
C17 C21 H21A 109.5 no
C17 C21 H21B 109.5 no
H21A C21 H21B 109.5 no
C17 C21 H21C 109.5 no
H21A C21 H21C 109.5 no
H21B C21 H21C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C9 1.2745(15) no
N1 C14 1.4229(15) no
C1 C10 1.3837(16) no
C1 C2 1.3953(16) no
C1 H1B 0.9500 no
C2 C3 1.3928(16) no
C2 H2A 0.9500 no
C3 C4 1.3966(17) no
C3 H3A 0.9500 no
C4 C11 1.3864(16) no
C4 H4A 0.9500 no
C5 C12 1.3880(15) no
C5 C6 1.3933(17) no
C5 H5A 0.9500 no
C6 C7 1.3893(18) no
C6 H6A 0.9500 no
C7 C8 1.3975(16) no
C7 H7A 0.9500 no
C8 C13 1.3902(16) no
C8 H8A 0.9500 no
C9 C10 1.4888(15) no
C9 C13 1.4982(15) no
C10 C11 1.4035(15) no
C11 C12 1.4714(16) no
C12 C13 1.4090(16) no
C14 C19 1.3890(17) no
C14 C15 1.3937(16) no
C15 C16 1.3922(16) no
C15 H15A 0.9500 no
C16 C17 1.4045(17) no
C16 C20 1.5061(16) no
C17 C18 1.3911(17) no
C17 C21 1.5059(16) no
C18 C19 1.3897(16) 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
C21 H21A 0.9800 no
C21 H21B 0.9800 no
C21 H21C 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 -0.09(17) no
C1 C2 C3 C4 0.09(18) no
C2 C3 C4 C11 0.16(17) no
C12 C5 C6 C7 -0.23(17) no
C5 C6 C7 C8 0.41(18) no
C6 C7 C8 C13 -0.19(17) no
C14 N1 C9 C10 178.03(9) no
C14 N1 C9 C13 -0.52(19) no
C2 C1 C10 C11 -0.16(16) no
C2 C1 C10 C9 -178.89(10) no
N1 C9 C10 C1 0.25(18) no
C13 C9 C10 C1 179.14(11) no
N1 C9 C10 C11 -178.60(10) no
C13 C9 C10 C11 0.29(11) no
C3 C4 C11 C10 -0.42(17) no
C3 C4 C11 C12 179.19(11) no
C1 C10 C11 C4 0.42(16) no
C9 C10 C11 C4 179.39(9) no
C1 C10 C11 C12 -179.27(10) no
C9 C10 C11 C12 -0.30(12) no
C6 C5 C12 C13 -0.14(16) no
C6 C5 C12 C11 179.70(11) no
C4 C11 C12 C5 0.7(2) no
C10 C11 C12 C5 -179.65(11) no
C4 C11 C12 C13 -179.45(11) no
C10 C11 C12 C13 0.20(12) no
C7 C8 C13 C12 -0.18(16) no
C7 C8 C13 C9 -179.54(11) no
C5 C12 C13 C8 0.35(16) no
C11 C12 C13 C8 -179.52(10) no
C5 C12 C13 C9 179.85(9) no
C11 C12 C13 C9 -0.01(12) no
N1 C9 C13 C8 -2.0(2) no
C10 C9 C13 C8 179.26(11) no
N1 C9 C13 C12 178.56(12) no
C10 C9 C13 C12 -0.16(11) no
C9 N1 C14 C19 -92.47(14) no
C9 N1 C14 C15 91.52(13) no
C19 C14 C15 C16 2.33(17) no
N1 C14 C15 C16 178.37(9) no
C14 C15 C16 C17 -1.15(16) no
C14 C15 C16 C20 -179.64(10) no
C15 C16 C17 C18 -0.53(16) no
C20 C16 C17 C18 177.95(11) no
C15 C16 C17 C21 -178.75(10) no
C20 C16 C17 C21 -0.27(16) no
C16 C17 C18 C19 1.04(17) no
C21 C17 C18 C19 179.26(11) no
C15 C14 C19 C18 -1.80(17) no
N1 C14 C19 C18 -177.84(10) no
C17 C18 C19 C14 0.13(17) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130678
