#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:41:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180350 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/19/7201989.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7201989
loop_
_publ_author_name
'Xin, Qian'
'Tao, Xu-Tang'
'Liu, Hui-Jun'
'Ren, Yan'
'Jiang, Min-Hua'
_publ_section_title
;
 Synthesis, structure and packing properties of three Tröger's base
 analogues containing substituted fluorene units
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1204
_journal_paper_doi               10.1039/b801899e
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C45 H54 N2'
_chemical_formula_sum            'C45 H54 N2'
_chemical_formula_weight         622.90
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 105.3380(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.6964(5)
_cell_length_b                   8.9890(2)
_cell_length_c                   15.7756(3)
_cell_measurement_reflns_used    4412
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.40
_cell_volume                     3650.89(13)
_computing_cell_refinement       'APEX2 Software Suite (Bruker,2005)'
_computing_data_collection       'APEX2 Software Suite (Bruker,2005)'
_computing_data_reduction        'APEX2 Software Suite (Bruker,2005)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'WINGX (Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare,1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13468
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0498
_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)+(0.0780P)²+1.3884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                3038
_reflns_number_total             4187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b801899e.txt
_cod_data_source_block           xinqian01
_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 
;
_cod_original_sg_symbol_H-M      'C2/c '
_cod_database_code               7201989
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29132(10) 0.6043(3) 0.28773(18) 0.0955(8) Uani 1 1 d . . .
H1A H 0.3190 0.6660 0.3206 0.143 Uiso 1 1 calc R . .
H1B H 0.2609 0.6640 0.2650 0.143 Uiso 1 1 calc R . .
H1C H 0.3016 0.5586 0.2399 0.143 Uiso 1 1 calc R . .
C2 C 0.27949(7) 0.4855(2) 0.34679(12) 0.0609(5) Uani 1 1 d . . .
H2A H 0.2518 0.4230 0.3127 0.073 Uiso 1 1 calc R . .
H2B H 0.2670 0.5325 0.3926 0.073 Uiso 1 1 calc R . .
C3 C 0.32562(6) 0.38843(18) 0.38915(11) 0.0526(4) Uani 1 1 d . . .
H3A H 0.3534 0.4508 0.4231 0.063 Uiso 1 1 calc R . .
H3B H 0.3380 0.3406 0.3434 0.063 Uiso 1 1 calc R . .
C4 C 0.31313(5) 0.26986(17) 0.44889(10) 0.0459(3) Uani 1 1 d . . .
H4A H 0.2849 0.2092 0.4147 0.055 Uiso 1 1 calc R . .
H4B H 0.3008 0.3187 0.4943 0.055 Uiso 1 1 calc R . .
C5 C 0.35851(5) 0.16625(16) 0.49357(9) 0.0424(3) Uani 1 1 d . . .
C6 C 0.33860(6) 0.04613(18) 0.54660(10) 0.0480(4) Uani 1 1 d . . .
H6A H 0.3263 0.0952 0.5920 0.058 Uiso 1 1 calc R . .
H6B H 0.3091 -0.0033 0.5076 0.058 Uiso 1 1 calc R . .
C7 C 0.37808(7) -0.0719(2) 0.58985(11) 0.0584(4) Uani 1 1 d . . .
H7A H 0.4065 -0.0242 0.6324 0.070 Uiso 1 1 calc R . .
H7B H 0.3922 -0.1172 0.5454 0.070 Uiso 1 1 calc R . .
C8 C 0.35529(9) -0.1938(2) 0.63604(14) 0.0769(6) Uani 1 1 d . . .
H8A H 0.3837 -0.2478 0.6750 0.092 Uiso 1 1 calc R . .
H8B H 0.3354 -0.1471 0.6722 0.092 Uiso 1 1 calc R . .
C9 C 0.32177(13) -0.3003(3) 0.5772(2) 0.1223(11) Uani 1 1 d . . .
H9A H 0.2919 -0.2495 0.5418 0.183 Uiso 1 1 calc R . .
H9B H 0.3108 -0.3759 0.6114 0.183 Uiso 1 1 calc R . .
H9C H 0.3406 -0.3453 0.5399 0.183 Uiso 1 1 calc R . .
C10 C 0.38310(6) 0.09475(16) 0.42681(9) 0.0445(3) Uani 1 1 d . . .
C11 C 0.36052(7) -0.00194(19) 0.35924(10) 0.0541(4) Uani 1 1 d . . .
H11 H 0.3257 -0.0281 0.3486 0.065 Uiso 1 1 calc R . .
C12 C 0.39070(8) -0.0591(2) 0.30775(11) 0.0635(5) Uani 1 1 d . . .
H12 H 0.3759 -0.1237 0.2619 0.076 Uiso 1 1 calc R . .
C13 C 0.44230(8) -0.0215(2) 0.32371(11) 0.0658(5) Uani 1 1 d . . .
H13 H 0.4620 -0.0613 0.2886 0.079 Uiso 1 1 calc R . .
C14 C 0.46548(7) 0.0748(2) 0.39131(10) 0.0570(4) Uani 1 1 d . . .
H14 H 0.5004 0.0995 0.4019 0.068 Uiso 1 1 calc R . .
C15 C 0.43551(6) 0.13351(17) 0.44287(9) 0.0454(3) Uani 1 1 d . . .
C16 C 0.44874(5) 0.23368(17) 0.51892(9) 0.0442(3) Uani 1 1 d . . .
C17 C 0.40458(5) 0.25319(16) 0.55011(9) 0.0426(3) Uani 1 1 d . . .
C18 C 0.40644(5) 0.34522(17) 0.62076(10) 0.0461(3) Uani 1 1 d . . .
H18 H 0.3770 0.3591 0.6407 0.055 Uiso 1 1 calc R . .
C19 C 0.45282(6) 0.41761(16) 0.66240(10) 0.0487(4) Uani 1 1 d . . .
C20 C 0.49773(6) 0.39205(17) 0.63411(10) 0.0498(4) Uani 1 1 d . . .
C21 C 0.49495(5) 0.30287(18) 0.56121(10) 0.0499(4) Uani 1 1 d . . .
H21 H 0.5242 0.2895 0.5407 0.060 Uiso 1 1 calc R . .
C23 C 0.5000 0.6141(3) 0.7500 0.0731(8) Uani 1 2 d S . .
H23A H 0.5009 0.6776 0.8001 0.088 Uiso 0.50 1 calc PR . .
H23B H 0.4991 0.6776 0.6999 0.088 Uiso 0.50 1 calc PR . .
C24 C 0.45039(6) 0.4564(2) 0.81483(11) 0.0595(5) Uani 1 1 d . . .
H24A H 0.4245 0.3781 0.8032 0.071 Uiso 1 1 calc R . .
H24B H 0.4395 0.5316 0.8503 0.071 Uiso 1 1 calc R . .
N1 N 0.45310(5) 0.52283(15) 0.73128(10) 0.0599(4) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 113.77(16) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 113.10(13) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 115.64(12) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
C10 C5 C17 101.06(11) . . ?
C10 C5 C4 111.65(11) . . ?
C17 C5 C4 111.79(12) . . ?
C10 C5 C6 110.66(12) . . ?
C17 C5 C6 112.36(11) . . ?
C4 C5 C6 109.17(11) . . ?
C7 C6 C5 115.66(12) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 C8 113.40(15) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 114.9(2) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 120.48(14) . . ?
C11 C10 C5 128.18(14) . . ?
C15 C10 C5 111.30(13) . . ?
C10 C11 C12 118.82(17) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.73(17) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.09(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 118.65(16) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C10 120.23(15) . . ?
C14 C15 C16 131.44(15) . . ?
C10 C15 C16 108.31(12) . . ?
C21 C16 C17 119.92(14) . . ?
C21 C16 C15 131.37(14) . . ?
C17 C16 C15 108.70(13) . . ?
C18 C17 C16 120.30(13) . . ?
C18 C17 C5 129.04(13) . . ?
C16 C17 C5 110.62(12) . . ?
C17 C18 C19 119.80(14) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 119.90(14) . . ?
C18 C19 N1 119.17(14) . . ?
C20 C19 N1 120.87(14) . . ?
C21 C20 C19 119.66(14) . . ?
C21 C20 C24 120.03(15) . 2_656 ?
C19 C20 C24 120.27(15) . 2_656 ?
C16 C21 C20 120.29(14) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
N1 C23 N1 111.60(18) . 2_656 ?
N1 C23 H23A 109.3 . . ?
N1 C23 H23A 109.3 2_656 . ?
N1 C23 H23B 109.3 . . ?
N1 C23 H23B 109.3 2_656 . ?
H23A C23 H23B 108.0 . . ?
N1 C24 C20 112.12(14) . 2_656 ?
N1 C24 H24A 109.2 . . ?
C20 C24 H24A 109.2 2_656 . ?
N1 C24 H24B 109.2 . . ?
C20 C24 H24B 109.2 2_656 . ?
H24A C24 H24B 107.9 . . ?
C19 N1 C23 110.79(13) . . ?
C19 N1 C24 114.79(13) . . ?
C23 N1 C24 106.90(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.505(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.513(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.517(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.5429(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.523(2) . ?
C5 C17 1.5291(19) . ?
C5 C6 1.544(2) . ?
C6 C7 1.524(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.529(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.462(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.384(2) . ?
C10 C15 1.398(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.466(2) . ?
C16 C21 1.385(2) . ?
C16 C17 1.404(2) . ?
C17 C18 1.378(2) . ?
C18 C19 1.399(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.404(2) . ?
C19 N1 1.439(2) . ?
C20 C21 1.388(2) . ?
C20 C24 1.520(2) 2_656 ?
C21 H21 0.9300 . ?
C23 N1 1.461(2) . ?
C23 N1 1.461(2) 2_656 ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N1 1.466(2) . ?
C24 C20 1.520(2) 2_656 ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 179.66(17) . . . . ?
C2 C3 C4 C5 179.53(13) . . . . ?
C3 C4 C5 C10 -53.49(17) . . . . ?
C3 C4 C5 C17 58.90(17) . . . . ?
C3 C4 C5 C6 -176.16(13) . . . . ?
C10 C5 C6 C7 52.74(17) . . . . ?
C17 C5 C6 C7 -59.39(17) . . . . ?
C4 C5 C6 C7 176.00(13) . . . . ?
C5 C6 C7 C8 -176.01(15) . . . . ?
C6 C7 C8 C9 74.0(2) . . . . ?
C17 C5 C10 C11 177.89(14) . . . . ?
C4 C5 C10 C11 -63.13(19) . . . . ?
C6 C5 C10 C11 58.68(19) . . . . ?
C17 C5 C10 C15 0.46(15) . . . . ?
C4 C5 C10 C15 119.44(13) . . . . ?
C6 C5 C10 C15 -118.75(13) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C5 C10 C11 C12 -177.44(14) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 0.5(2) . . . . ?
C13 C14 C15 C16 178.49(15) . . . . ?
C11 C10 C15 C14 -0.2(2) . . . . ?
C5 C10 C15 C14 177.41(13) . . . . ?
C11 C10 C15 C16 -178.69(13) . . . . ?
C5 C10 C15 C16 -1.03(16) . . . . ?
C14 C15 C16 C21 1.7(3) . . . . ?
C10 C15 C16 C21 179.88(15) . . . . ?
C14 C15 C16 C17 -176.99(15) . . . . ?
C10 C15 C16 C17 1.22(16) . . . . ?
C21 C16 C17 C18 2.3(2) . . . . ?
C15 C16 C17 C18 -178.81(13) . . . . ?
C21 C16 C17 C5 -179.78(13) . . . . ?
C15 C16 C17 C5 -0.93(16) . . . . ?
C10 C5 C17 C18 177.96(14) . . . . ?
C4 C5 C17 C18 59.08(19) . . . . ?
C6 C5 C17 C18 -64.07(19) . . . . ?
C10 C5 C17 C16 0.31(15) . . . . ?
C4 C5 C17 C16 -118.57(13) . . . . ?
C6 C5 C17 C16 118.28(13) . . . . ?
C16 C17 C18 C19 -1.0(2) . . . . ?
C5 C17 C18 C19 -178.46(13) . . . . ?
C17 C18 C19 C20 -2.3(2) . . . . ?
C17 C18 C19 N1 174.86(13) . . . . ?
C18 C19 C20 C21 4.3(2) . . . . ?
N1 C19 C20 C21 -172.80(13) . . . . ?
C18 C19 C20 C24 -173.16(13) . . . 2_656 ?
N1 C19 C20 C24 9.7(2) . . . 2_656 ?
C17 C16 C21 C20 -0.3(2) . . . . ?
C15 C16 C21 C20 -178.84(14) . . . . ?
C19 C20 C21 C16 -3.0(2) . . . . ?
C24 C20 C21 C16 174.48(13) 2_656 . . . ?
C18 C19 N1 C23 -164.90(13) . . . . ?
C20 C19 N1 C23 12.24(19) . . . . ?
C18 C19 N1 C24 73.91(17) . . . . ?
C20 C19 N1 C24 -108.96(17) . . . . ?
N1 C23 N1 C19 -53.71(9) 2_656 . . . ?
N1 C23 N1 C24 72.04(9) 2_656 . . . ?
C20 C24 N1 C19 77.24(17) 2_656 . . . ?
C20 C24 N1 C23 -46.06(17) 2_656 . . . ?
