#------------------------------------------------------------------------------
#$Date: 2021-09-18 05:06:16 +0300 (Sat, 18 Sep 2021) $
#$Revision: 269204 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243922.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_2243922
loop_
_publ_author_name
'Seidel, Pierre'
'Schwarzer, Anke'
'Mazik, Monika'
_publ_section_title
;
 Crystal structure of 9,9-diethyl-9H-fluorene-2,4,7-tricarbaldehyde
;
_journal_coeditor_code           ZQ2265
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1
_journal_page_last               0
_journal_paper_doi               10.1107/S2056989021009464
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C20 H18 O3'
_chemical_formula_moiety         'C20 H18 O3'
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
_chemical_name_systematic
;
9,9-Diethylfluorene-2,4,7-tricarbaldehyde
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.146(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6595(9)
_cell_length_b                   13.1466(14)
_cell_length_c                   7.6834(15)
_cell_measurement_reflns_used    6293
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.89
_cell_volume                     1579.4(4)
_computing_cell_refinement
;
X-AREA (Stoe, 2009)
;
_computing_data_collection
;
X-AREA (Stoe, 2009)
;
_computing_data_reduction
;
X-RED (Stoe, 2009)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010),
and shelXle (Hübschle et al.,  2011)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13951
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         3.032
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       piece
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         13951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0713P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                8830
_reflns_number_total             13951
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zq2265sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243922
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.51535(14) 0.34892(18) 0.5435(3) 0.0532(7) Uani d 1 . .
O O2 0.15641(16) 0.18707(17) -0.0059(3) 0.0604(7) Uani d 1 . .
O O3 0.03712(16) 0.7414(2) -0.2592(4) 0.0713(8) Uani d 1 . .
C C1 0.37790(18) 0.4293(2) 0.3116(3) 0.0322(7) Uani d 1 . .
H H1 0.414572 0.480263 0.361567 0.039 Uiso calc 1 . .
C C2 0.39372(18) 0.3258(2) 0.3466(3) 0.0316(7) Uani d 1 . .
C C3 0.33905(17) 0.2531(2) 0.2722(4) 0.0330(6) Uani d 1 . .
H H3 0.350875 0.183387 0.295850 0.040 Uiso calc 1 . .
C C4 0.26770(17) 0.2774(2) 0.1647(3) 0.0313(7) Uani d 1 . .
C C5 0.11308(18) 0.4025(2) -0.0802(4) 0.0372(7) Uani d 1 . .
H H5 0.099564 0.332138 -0.087467 0.045 Uiso calc 1 . .
C C6 0.06274(19) 0.4738(2) -0.1701(4) 0.0412(8) Uani d 1 . .
H H6 0.014947 0.451369 -0.241394 0.049 Uiso calc 1 . .
C C7 0.08030(19) 0.5775(2) -0.1586(4) 0.0385(7) Uani d 1 . .
C C8 0.15063(18) 0.6120(2) -0.0543(4) 0.0364(7) Uani d 1 . .
H H8 0.162721 0.682613 -0.044365 0.044 Uiso calc 1 . .
C C9 0.28194(18) 0.5627(2) 0.1500(4) 0.0313(7) Uani d 1 . .
C C10 0.30798(17) 0.4554(2) 0.2032(3) 0.0294(6) Uani d 1 . .
C C11 0.25144(17) 0.3818(2) 0.1286(3) 0.0291(6) Uani d 1 . .
C C12 0.18436(17) 0.4364(2) 0.0215(3) 0.0305(6) Uani d 1 . .
C C13 0.20206(18) 0.5414(2) 0.0338(3) 0.0311(7) Uani d 1 . .
C C14 0.46610(18) 0.2932(2) 0.4635(4) 0.0379(7) Uani d 1 . .
H H14 0.474848 0.222039 0.477297 0.045 Uiso calc 1 . .
C C15 0.2180(2) 0.1882(2) 0.0975(4) 0.0436(8) Uani d 1 . .
H H15 0.236754 0.123771 0.140831 0.052 Uiso calc 1 . .
C C16 0.0245(2) 0.6512(3) -0.2560(5) 0.0535(9) Uani d 1 . .
H H16 -0.024467 0.625546 -0.320103 0.064 Uiso calc 1 . .
C C17 0.26251(19) 0.6290(2) 0.3086(4) 0.0366(7) Uani d 1 . .
H H17A 0.315855 0.636730 0.382697 0.044 Uiso calc 1 . .
H H17B 0.245393 0.697499 0.266210 0.044 Uiso calc 1 . .
C C18 0.1931(2) 0.5885(2) 0.4212(4) 0.0466(8) Uani d 1 . .
H H18A 0.190690 0.630388 0.526375 0.070 Uiso calc 1 . .
H H18B 0.206083 0.518019 0.454380 0.070 Uiso calc 1 . .
H H18C 0.137719 0.591187 0.355334 0.070 Uiso calc 1 . .
C C19 0.35203(19) 0.6155(2) 0.0494(4) 0.0388(7) Uani d 1 . .
H H19A 0.331460 0.684240 0.015221 0.047 Uiso calc 1 . .
H H19B 0.403150 0.624283 0.129659 0.047 Uiso calc 1 . .
C C20 0.3791(2) 0.5611(3) -0.1127(4) 0.0516(9) Uani d 1 . .
H H20A 0.419668 0.603613 -0.172536 0.077 Uiso calc 1 . .
H H20B 0.328650 0.548144 -0.190883 0.077 Uiso calc 1 . .
H H20C 0.406310 0.496296 -0.079554 0.077 Uiso calc 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 C1 C2 . . 118.8(2) ?
C10 C1 H1 . . 120.6 ?
C2 C1 H1 . . 120.6 ?
C3 C2 C1 . . 119.4(2) ?
C3 C2 C14 . . 119.2(3) ?
C1 C2 C14 . . 121.4(2) ?
C2 C3 C4 . . 123.0(3) ?
C2 C3 H3 . . 118.5 ?
C4 C3 H3 . . 118.5 ?
C3 C4 C11 . . 117.9(2) ?
C3 C4 C15 . . 114.4(3) ?
C11 C4 C15 . . 127.7(2) ?
C6 C5 C12 . . 118.5(3) ?
C6 C5 H5 . . 120.7 ?
C12 C5 H5 . . 120.7 ?
C5 C6 C7 . . 121.8(2) ?
C5 C6 H6 . . 119.1 ?
C7 C6 H6 . . 119.1 ?
C6 C7 C8 . . 119.9(3) ?
C6 C7 C16 . . 120.0(3) ?
C8 C7 C16 . . 120.1(3) ?
C13 C8 C7 . . 118.8(3) ?
C13 C8 H8 . . 120.6 ?
C7 C8 H8 . . 120.6 ?
C10 C9 C13 . . 100.8(2) ?
C10 C9 C19 . . 111.4(2) ?
C13 C9 C19 . . 111.9(2) ?
C10 C9 C17 . . 112.0(2) ?
C13 C9 C17 . . 112.1(2) ?
C19 C9 C17 . . 108.6(2) ?
C1 C10 C11 . . 122.2(2) ?
C1 C10 C9 . . 125.8(2) ?
C11 C10 C9 . . 112.0(2) ?
C10 C11 C4 . . 118.8(2) ?
C10 C11 C12 . . 107.6(2) ?
C4 C11 C12 . . 133.6(2) ?
C5 C12 C13 . . 119.8(2) ?
C5 C12 C11 . . 132.4(2) ?
C13 C12 C11 . . 107.8(2) ?
C8 C13 C12 . . 121.2(2) ?
C8 C13 C9 . . 127.0(2) ?
C12 C13 C9 . . 111.8(2) ?
O1 C14 C2 . . 125.7(3) ?
O1 C14 H14 . . 117.2 ?
C2 C14 H14 . . 117.2 ?
O2 C15 C4 . . 128.2(3) ?
O2 C15 H15 . . 115.9 ?
C4 C15 H15 . . 115.9 ?
O3 C16 C7 . . 124.2(3) ?
O3 C16 H16 . . 117.9 ?
C7 C16 H16 . . 117.9 ?
C18 C17 C9 . . 115.5(2) ?
C18 C17 H17A . . 108.4 ?
C9 C17 H17A . . 108.4 ?
C18 C17 H17B . . 108.4 ?
C9 C17 H17B . . 108.4 ?
H17A C17 H17B . . 107.5 ?
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 C9 . . 116.0(2) ?
C20 C19 H19A . . 108.3 ?
C9 C19 H19A . . 108.3 ?
C20 C19 H19B . . 108.3 ?
C9 C19 H19B . . 108.3 ?
H19A C19 H19B . . 107.4 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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
O1 C14 . 1.207(3) ?
O2 C15 . 1.216(3) ?
O3 C16 . 1.203(4) ?
C1 C10 . 1.382(4) ?
C1 C2 . 1.406(4) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.386(4) ?
C2 C14 . 1.471(4) ?
C3 C4 . 1.390(4) ?
C3 H3 . 0.9500 ?
C4 C11 . 1.421(4) ?
C4 C15 . 1.484(4) ?
C5 C6 . 1.384(4) ?
C5 C12 . 1.400(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.393(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.401(4) ?
C7 C16 . 1.479(4) ?
C8 C13 . 1.381(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.518(4) ?
C9 C13 . 1.523(4) ?
C9 C19 . 1.542(4) ?
C9 C17 . 1.542(4) ?
C10 C11 . 1.411(4) ?
C11 C12 . 1.483(4) ?
C12 C13 . 1.410(4) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 C18 . 1.522(5) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 C20 . 1.517(5) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
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
_geom_hbond_publ_flag
C1 H1 O1 3_666 0.95 2.59 3.512(4) 164.7 yes
C5 H5 O2 . 0.95 2.18 2.961(4) 138.4 yes
C5 H5 O3 2_544 0.95 2.67 3.350(4) 129.2 yes
C16 H16 O2 2_554 0.95 2.53 3.321(4) 140.6 yes
C17 H17A O1 3_666 0.99 2.68 3.611(4) 157.0 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -0.1(4) ?
C10 C1 C2 C14 . . . . -178.8(3) ?
C1 C2 C3 C4 . . . . -0.7(4) ?
C14 C2 C3 C4 . . . . 178.0(3) ?
C2 C3 C4 C11 . . . . 0.8(4) ?
C2 C3 C4 C15 . . . . 179.6(3) ?
C12 C5 C6 C7 . . . . -1.3(5) ?
C5 C6 C7 C8 . . . . 0.1(5) ?
C5 C6 C7 C16 . . . . -179.6(3) ?
C6 C7 C8 C13 . . . . 0.9(5) ?
C16 C7 C8 C13 . . . . -179.4(3) ?
C2 C1 C10 C11 . . . . 0.9(4) ?
C2 C1 C10 C9 . . . . -179.3(3) ?
C13 C9 C10 C1 . . . . -179.8(3) ?
C19 C9 C10 C1 . . . . 61.4(3) ?
C17 C9 C10 C1 . . . . -60.5(4) ?
C13 C9 C10 C11 . . . . 0.0(3) ?
C19 C9 C10 C11 . . . . -118.8(2) ?
C17 C9 C10 C11 . . . . 119.3(3) ?
C1 C10 C11 C4 . . . . -0.8(4) ?
C9 C10 C11 C4 . . . . 179.4(3) ?
C1 C10 C11 C12 . . . . 179.7(3) ?
C9 C10 C11 C12 . . . . -0.1(3) ?
C3 C4 C11 C10 . . . . -0.1(4) ?
C15 C4 C11 C10 . . . . -178.6(3) ?
C3 C4 C11 C12 . . . . 179.2(3) ?
C15 C4 C11 C12 . . . . 0.7(5) ?
C6 C5 C12 C13 . . . . 1.5(4) ?
C6 C5 C12 C11 . . . . -178.3(3) ?
C10 C11 C12 C5 . . . . 180.0(3) ?
C4 C11 C12 C5 . . . . 0.6(6) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C4 C11 C12 C13 . . . . -179.3(3) ?
C7 C8 C13 C12 . . . . -0.6(5) ?
C7 C8 C13 C9 . . . . 178.7(3) ?
C5 C12 C13 C8 . . . . -0.6(4) ?
C11 C12 C13 C8 . . . . 179.3(3) ?
C5 C12 C13 C9 . . . . -180.0(3) ?
C11 C12 C13 C9 . . . . -0.1(3) ?
C10 C9 C13 C8 . . . . -179.4(3) ?
C19 C9 C13 C8 . . . . -60.9(4) ?
C17 C9 C13 C8 . . . . 61.4(4) ?
C10 C9 C13 C12 . . . . 0.0(3) ?
C19 C9 C13 C12 . . . . 118.5(3) ?
C17 C9 C13 C12 . . . . -119.2(3) ?
C3 C2 C14 O1 . . . . -175.8(3) yes
C1 C2 C14 O1 . . . . 2.9(5) yes
C3 C4 C15 O2 . . . . -175.4(3) yes
C11 C4 C15 O2 . . . . 3.2(5) yes
C6 C7 C16 O3 . . . . -176.7(4) yes
C8 C7 C16 O3 . . . . 3.5(6) yes
C10 C9 C17 C18 . . . . -57.6(3) ?
C13 C9 C17 C18 . . . . 54.8(3) ?
C19 C9 C17 C18 . . . . 179.0(2) ?
C10 C9 C19 C20 . . . . 56.6(3) ?
C13 C9 C19 C20 . . . . -55.3(3) ?
C17 C9 C19 C20 . . . . -179.6(2) ?

_cod_database_fobs_code 2243922
