#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/84/2208459.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_2208459
loop_
_publ_author_name
'Hu, Wei-Bing'
'Liu, Hong-Xia'
'Tian, Da-Ting'
'Liu, Cheng-Mei'
'Liu, Zu-Li'
_publ_section_title
;
 9,9-Bis(ethoxycarbonylethyl)-9H-fluorene
;
_journal_coeditor_code           XU2002
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1105
_journal_page_last               o1106
_journal_paper_doi               10.1107/S1600536806005733
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C23 H26 O4'
_chemical_formula_moiety         'C23 H26 O4'
_chemical_formula_sum            'C23 H26 O4'
_chemical_formula_weight         366.44
_chemical_melting_point          377
_chemical_name_common
;
9,9-Bis(ethoxycarbonylethyl)-9H-fluorene
;
_chemical_name_systematic
;
diethyl 3,3'-(9H-fluorene-9,9-diyl)dipropionate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.8464(7)
_cell_length_b                   16.9377(11)
_cell_length_c                   22.2437(14)
_cell_measurement_reflns_used    6837
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      20.7
_cell_measurement_theta_min      2.4
_cell_volume                     4086.5(5)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.072
_diffrn_reflns_av_sigmaI/netI    0.032
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            40279
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.060
_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)+(0.0954P)²+0.5495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.158
_refine_ls_wR_factor_ref         0.172
_reflns_number_gt                2931
_reflns_number_total             4005
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2002.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2208459
_cod_database_fobs_code          2208459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_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
C C1 0.62224(17) 0.14453(11) 0.37348(8) 0.0435(4) Uani d . 1
C C2 0.5983(2) 0.07400(12) 0.34449(9) 0.0562(5) Uani d . 1
H H2 0.5360 0.0407 0.3580 0.067 Uiso calc R 1
C C3 0.6689(3) 0.05402(14) 0.29488(11) 0.0706(7) Uani d . 1
H H3 0.6533 0.0069 0.2749 0.085 Uiso calc R 1
C C4 0.7612(2) 0.10230(16) 0.27476(10) 0.0737(7) Uani d . 1
H H4 0.8077 0.0874 0.2415 0.088 Uiso calc R 1
C C5 0.7856(2) 0.17245(15) 0.30314(10) 0.0640(6) Uani d . 1
H H5 0.8483 0.2052 0.2893 0.077 Uiso calc R 1
C C6 0.71564(17) 0.19399(11) 0.35273(9) 0.0472(5) Uani d . 1
C C7 0.71827(17) 0.26470(11) 0.39067(9) 0.0477(5) Uani d . 1
C C8 0.7916(2) 0.33230(13) 0.38851(12) 0.0662(6) Uani d . 1
H H8 0.8524 0.3377 0.3593 0.079 Uiso calc R 1
C C9 0.7723(3) 0.39087(14) 0.43034(13) 0.0749(7) Uani d . 1
H H9 0.8214 0.4359 0.4296 0.090 Uiso calc R 1
C C10 0.6823(3) 0.38404(14) 0.47282(12) 0.0723(7) Uani d . 1
H H10 0.6700 0.4248 0.5002 0.087 Uiso calc R 1
C C11 0.6090(2) 0.31715(12) 0.47568(10) 0.0584(6) Uani d . 1
H H11 0.5485 0.3124 0.5051 0.070 Uiso calc R 1
C C12 0.62707(17) 0.25799(11) 0.43443(8) 0.0438(4) Uani d . 1
C C13 0.55825(16) 0.17990(10) 0.42791(8) 0.0425(4) Uani d . 1
C C14 0.57278(18) 0.12776(12) 0.48435(8) 0.0483(5) Uani d . 1
H H14A 0.5304 0.1530 0.5176 0.058 Uiso calc R 1
H H14B 0.5326 0.0775 0.4770 0.058 Uiso calc R 1
C C15 0.70480(18) 0.11241(12) 0.50266(9) 0.0511(5) Uani d . 1
H H15A 0.7470 0.0862 0.4698 0.061 Uiso calc R 1
H H15B 0.7456 0.1626 0.5095 0.061 Uiso calc R 1
C C16 0.7165(2) 0.06299(11) 0.55797(9) 0.0508(5) Uani d . 1
C C17 0.8568(3) 0.00183(16) 0.62486(11) 0.0798(8) Uani d . 1
H H17A 0.8045 -0.0446 0.6241 0.096 Uiso calc R 1
H H17B 0.8387 0.0315 0.6611 0.096 Uiso calc R 1
C C18 0.9859(3) -0.0216(2) 0.62445(16) 0.1150(12) Uani d . 1
H H18A 1.0036 -0.0498 0.5880 0.172 Uiso calc R 1
H H18B 1.0023 -0.0551 0.6584 0.172 Uiso calc R 1
H H18C 1.0371 0.0245 0.6267 0.172 Uiso calc R 1
C C19 0.41959(17) 0.19254(12) 0.41660(9) 0.0502(5) Uani d . 1
H H19A 0.3814 0.1416 0.4094 0.060 Uiso calc R 1
H H19B 0.3828 0.2147 0.4526 0.060 Uiso calc R 1
C C20 0.39113(18) 0.24625(13) 0.36412(9) 0.0551(5) Uani d . 1
H H20A 0.4237 0.2984 0.3725 0.066 Uiso calc R 1
H H20B 0.4325 0.2263 0.3286 0.066 Uiso calc R 1
C C21 0.2565(2) 0.25268(15) 0.35156(10) 0.0607(6) Uani d . 1
C C22 0.1039(2) 0.31390(19) 0.29289(16) 0.0952(9) Uani d . 1
H H22A 0.0786 0.2669 0.2712 0.114 Uiso calc R 1
H H22B 0.0528 0.3188 0.3285 0.114 Uiso calc R 1
C C23 0.0882(3) 0.3820(2) 0.25546(16) 0.1120(11) Uani d . 1
H H23A 0.1125 0.4284 0.2772 0.168 Uiso calc R 1
H H23B 0.0032 0.3865 0.2439 0.168 Uiso calc R 1
H H23C 0.1383 0.3767 0.2201 0.168 Uiso calc R 1
O O1 0.63198(16) 0.03670(11) 0.58596(8) 0.0864(6) Uani d . 1
O O2 0.83327(14) 0.05025(8) 0.57230(6) 0.0616(4) Uani d . 1
O O3 0.17811(17) 0.21310(15) 0.37423(10) 0.1171(9) Uani d . 1
O O4 0.23281(13) 0.30693(9) 0.31032(8) 0.0700(5) Uani d . 1
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'
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
C2 C1 C6 120.12(18)
C2 C1 C13 128.82(17)
C6 C1 C13 111.05(16)
C1 C2 C3 118.6(2)
C1 C2 H2 120.7
C3 C2 H2 120.7
C4 C3 C2 121.3(2)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.6(2)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 119.2(2)
C4 C5 H5 120.4
C6 C5 H5 120.4
C5 C6 C1 120.2(2)
C5 C6 C7 131.45(19)
C1 C6 C7 108.35(16)
C12 C7 C8 119.7(2)
C12 C7 C6 108.78(16)
C8 C7 C6 131.5(2)
C9 C8 C7 118.8(2)
C9 C8 H8 120.6
C7 C8 H8 120.6
C10 C9 C8 121.1(2)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C11 120.8(2)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 119.0(2)
C12 C11 H11 120.5
C10 C11 H11 120.5
C11 C12 C7 120.60(18)
C11 C12 C13 128.80(18)
C7 C12 C13 110.60(16)
C1 C13 C12 101.20(14)
C1 C13 C19 111.78(15)
C12 C13 C19 111.89(15)
C1 C13 C14 112.10(15)
C12 C13 C14 111.64(15)
C19 C13 C14 108.20(14)
C15 C14 C13 114.49(15)
C15 C14 H14A 108.6
C13 C14 H14A 108.6
C15 C14 H14B 108.6
C13 C14 H14B 108.6
H14A C14 H14B 107.6
C16 C15 C14 113.51(16)
C16 C15 H15A 108.9
C14 C15 H15A 108.9
C16 C15 H15B 108.9
C14 C15 H15B 108.9
H15A C15 H15B 107.7
O1 C16 O2 123.22(19)
O1 C16 C15 125.0(2)
O2 C16 C15 111.78(17)
O2 C17 C18 108.6(2)
O2 C17 H17A 110.0
C18 C17 H17A 110.0
O2 C17 H17B 110.0
C18 C17 H17B 110.0
H17A C17 H17B 108.4
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C20 C19 C13 114.16(15)
C20 C19 H19A 108.7
C13 C19 H19A 108.7
C20 C19 H19B 108.7
C13 C19 H19B 108.7
H19A C19 H19B 107.6
C21 C20 C19 112.88(17)
C21 C20 H20A 109.0
C19 C20 H20A 109.0
C21 C20 H20B 109.0
C19 C20 H20B 109.0
H20A C20 H20B 107.8
O3 C21 O4 123.0(2)
O3 C21 C20 125.3(2)
O4 C21 C20 111.76(19)
C23 C22 O4 109.5(2)
C23 C22 H22A 109.8
O4 C22 H22A 109.8
C23 C22 H22B 109.8
O4 C22 H22B 109.8
H22A C22 H22B 108.2
C22 C23 H23A 109.5
C22 C23 H23B 109.5
H23A C23 H23B 109.5
C22 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C16 O2 C17 117.05(18)
C21 O4 C22 115.30(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.382(3) ?
C1 C6 1.393(3) ?
C1 C13 1.519(3) yes
C2 C3 1.386(3) ?
C2 H2 0.9300 ?
C3 C4 1.367(3) ?
C3 H3 0.9300 ?
C4 C5 1.371(3) ?
C4 H4 0.9300 ?
C5 C6 1.388(3) ?
C5 H5 0.9300 ?
C6 C7 1.465(3) ?
C7 C12 1.392(3) ?
C7 C8 1.395(3) ?
C8 C9 1.376(3) ?
C8 H8 0.9300 ?
C9 C10 1.363(4) ?
C9 H9 0.9300 ?
C10 C11 1.386(3) ?
C10 H10 0.9300 ?
C11 C12 1.373(3) ?
C11 H11 0.9300 ?
C12 C13 1.526(3) yes
C13 C19 1.540(3) ?
C13 C14 1.543(2) ?
C14 C15 1.511(3) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C16 1.493(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 O1 1.194(2) yes
C16 O2 1.324(2) yes
C17 O2 1.451(2) yes
C17 C18 1.456(4) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
C19 C20 1.512(3) ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 C21 1.491(3) ?
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C21 O3 1.194(3) yes
C21 O4 1.324(3) yes
C22 C23 1.433(4) ?
C22 O4 1.456(3) yes
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
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
C2 H2 O1 5_656 0.93 2.57 3.485(3) 169
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 0.1(3) ?
C13 C1 C2 C3 179.53(19) ?
C1 C2 C3 C4 0.4(3) ?
C2 C3 C4 C5 -0.5(4) ?
C3 C4 C5 C6 0.1(4) ?
C4 C5 C6 C1 0.4(3) ?
C4 C5 C6 C7 -178.4(2) ?
C2 C1 C6 C5 -0.5(3) ?
C13 C1 C6 C5 -179.99(18) ?
C2 C1 C6 C7 178.58(16) ?
C13 C1 C6 C7 -1.0(2) ?
C5 C6 C7 C12 179.1(2) ?
C1 C6 C7 C12 0.2(2) ?
C5 C6 C7 C8 0.3(4) ?
C1 C6 C7 C8 -178.6(2) ?
C12 C7 C8 C9 0.5(3) ?
C6 C7 C8 C9 179.2(2) ?
C7 C8 C9 C10 -0.9(4) ?
C8 C9 C10 C11 1.1(4) ?
C9 C10 C11 C12 -0.9(3) ?
C10 C11 C12 C7 0.5(3) ?
C10 C11 C12 C13 -179.33(19) ?
C8 C7 C12 C11 -0.3(3) ?
C6 C7 C12 C11 -179.32(17) ?
C8 C7 C12 C13 179.56(17) ?
C6 C7 C12 C13 0.6(2) ?
C2 C1 C13 C12 -178.27(18) ?
C6 C1 C13 C12 1.22(19) ?
C2 C1 C13 C19 -59.0(2) ?
C6 C1 C13 C19 120.45(17) ?
C2 C1 C13 C14 62.6(2) ?
C6 C1 C13 C14 -117.87(17) ?
C11 C12 C13 C1 178.81(18) ?
C7 C12 C13 C1 -1.07(18) ?
C11 C12 C13 C19 59.7(2) ?
C7 C12 C13 C19 -120.22(17) ?
C11 C12 C13 C14 -61.8(2) ?
C7 C12 C13 C14 118.35(17) ?
C1 C13 C14 C15 58.4(2) ?
C12 C13 C14 C15 -54.4(2) ?
C19 C13 C14 C15 -177.91(17) ?
C13 C14 C15 C16 179.02(16) y
C14 C15 C16 O1 0.5(3) ?
C14 C15 C16 O2 179.46(17) y
C1 C13 C19 C20 -59.0(2) ?
C12 C13 C19 C20 53.7(2) ?
C14 C13 C19 C20 177.12(16) ?
C13 C19 C20 C21 175.83(18) y
C19 C20 C21 O3 -9.2(4) ?
C19 C20 C21 O4 172.54(18) y
O1 C16 O2 C17 -0.1(3) ?
C15 C16 O2 C17 -179.10(18) ?
C18 C17 O2 C16 165.8(2) y
O3 C21 O4 C22 -1.7(4) ?
C20 C21 O4 C22 176.7(2) ?
C23 C22 O4 C21 171.1(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 31124
