#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/22/4112261.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_4112261
loop_
_publ_author_name
'Shinji Nomura'
'Takahito Itoh'
'Hirofumi Nakasho'
'Takahiro Uno'
'Masataka Kubo'
'Kazuki Sada'
'Katsunari Inoue'
'Mikiji Miyata'
_publ_section_title
;
 Crystal Structures and Topochemical Polymerizations of
 7,7,8,8-Tetrakis(alkoxycarbonyl)quinodimethanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2035
_journal_page_last               2041
_journal_paper_doi               10.1021/ja0386086
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C20 H16 O4 '
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 92.459(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8775(8)
_cell_length_b                   7.9949(3)
_cell_length_c                   18.0881(9)
_cell_measurement_reflns_used    1113
_cell_measurement_temperature    204.2
_cell_measurement_theta_max      67.5
_cell_measurement_theta_min      6.5
_cell_volume                     1571.57(15)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9237
_diffrn_measured_fraction_theta_max 0.9237
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6817
_diffrn_reflns_theta_full        68.14
_diffrn_reflns_theta_max         68.14
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       chunk
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.862
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2652
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05500(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1506
_reflns_number_gt                2276
_reflns_number_total             2652
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja0386086si20030919_041918.cif
_cod_data_source_block           BnCQ
_cod_original_cell_volume        1571.6(2)
_cod_original_formula_sum        'C20 H16 O4 '
_cod_database_code               4112261
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
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_calc_flag
O(1) O 0.3502(1) -0.0754(2) 0.93873(9) 0.0488(4) Uani 1.00 d
O(2) O 0.3822(1) 0.1706(2) 0.88207(8) 0.0403(4) Uani 1.00 d
O(3) O 0.0936(2) 0.3475(2) 0.84565(9) 0.0489(4) Uani 1.00 d
O(4) O 0.1766(1) 0.1560(2) 0.77220(7) 0.0404(4) Uani 1.00 d
C(1) C 0.0928(2) 0.0482(2) 0.9488(1) 0.0336(5) Uani 1.00 d
C(2) C -0.0362(2) 0.0942(3) 0.9377(1) 0.0374(5) Uani 1.00 d
C(3) C -0.1223(2) 0.0493(3) 0.9850(1) 0.0369(5) Uani 1.00 d
C(4) C 0.1784(2) 0.0980(2) 0.8999(1) 0.0328(5) Uani 1.00 d
C(5) C 0.3112(2) 0.0499(3) 0.9094(1) 0.0355(5) Uani 1.00 d
C(6) C 0.5146(2) 0.1542(3) 0.8957(1) 0.0463(6) Uani 1.00 d
C(7) C 0.5807(2) 0.1597(2) 0.8244(1) 0.0344(5) Uani 1.00 d
C(8) C 0.5408(2) 0.0672(3) 0.7633(1) 0.0424(6) Uani 1.00 d
C(9) C 0.6081(2) 0.0680(3) 0.7002(1) 0.0532(7) Uani 1.00 d
C(10) C 0.7156(2) 0.1590(3) 0.6974(1) 0.0529(7) Uani 1.00 d
C(11) C 0.7556(2) 0.2522(3) 0.7579(1) 0.0484(6) Uani 1.00 d
C(12) C 0.6881(2) 0.2521(3) 0.8213(1) 0.0395(5) Uani 1.00 d
C(13) C 0.1447(2) 0.2162(3) 0.8378(1) 0.0340(5) Uani 1.00 d
C(14) C 0.1463(2) 0.2662(3) 0.7092(1) 0.0489(6) Uani 1.00 d
C(15) C 0.1979(2) 0.1913(3) 0.6415(1) 0.0370(5) Uani 1.00 d
C(16) C 0.1255(2) 0.0947(3) 0.5929(1) 0.0447(6) Uani 1.00 d
C(17) C 0.1745(3) 0.0314(3) 0.5292(1) 0.0541(7) Uani 1.00 d
C(18) C 0.2946(3) 0.0621(3) 0.5136(1) 0.0539(7) Uani 1.00 d
C(19) C 0.3676(2) 0.1565(3) 0.5615(1) 0.0531(7) Uani 1.00 d
C(20) C 0.3195(2) 0.2211(3) 0.6248(1) 0.0449(6) Uani 1.00 d
H(1) H -0.0608 0.1582 0.8953 0.0444 Uiso 1.00 calc
H(2) H -0.2057 0.0821 0.9757 0.0440 Uiso 1.00 calc
H(3) H 0.5434 0.2433 0.9267 0.0560 Uiso 1.00 calc
H(4) H 0.5318 0.0505 0.9198 0.0560 Uiso 1.00 calc
H(5) H 0.4675 0.0027 0.7647 0.0500 Uiso 1.00 calc
H(6) H 0.5802 0.0040 0.6583 0.0628 Uiso 1.00 calc
H(7) H 0.7618 0.1587 0.6539 0.0628 Uiso 1.00 calc
H(8) H 0.8289 0.3163 0.7561 0.0571 Uiso 1.00 calc
H(9) H 0.7164 0.3155 0.8633 0.0467 Uiso 1.00 calc
H(10) H 0.0593 0.2756 0.7025 0.0577 Uiso 1.00 calc
H(11) H 0.1809 0.3732 0.7179 0.0577 Uiso 1.00 calc
H(12) H 0.0422 0.0727 0.6032 0.0528 Uiso 1.00 calc
H(13) H 0.1245 -0.0347 0.4962 0.0643 Uiso 1.00 calc
H(14) H 0.3272 0.0191 0.4695 0.0648 Uiso 1.00 calc
H(15) H 0.4510 0.1776 0.5508 0.0631 Uiso 1.00 calc
H(16) H 0.3704 0.2867 0.6575 0.0536 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(5) O(2) C(6) 117.0(2) 1_555 1_555 yes
C(13) O(4) C(14) 114.5(2) 1_555 1_555 yes
C(2) C(1) C(3) 115.3(2) 1_555 3_557 yes
C(2) C(1) C(4) 121.0(2) 1_555 1_555 yes
C(3) C(1) C(4) 123.7(2) 3_557 1_555 yes
C(1) C(2) C(3) 122.5(2) 1_555 1_555 yes
C(1) C(3) C(2) 122.2(2) 3_557 1_555 yes
C(1) C(4) C(5) 122.1(2) 1_555 1_555 yes
C(1) C(4) C(13) 121.0(2) 1_555 1_555 yes
C(5) C(4) C(13) 116.7(2) 1_555 1_555 yes
O(1) C(5) O(2) 124.3(2) 1_555 1_555 yes
O(1) C(5) C(4) 125.8(2) 1_555 1_555 yes
O(2) C(5) C(4) 109.9(2) 1_555 1_555 yes
O(2) C(6) C(7) 111.0(2) 1_555 1_555 yes
C(6) C(7) C(8) 121.6(2) 1_555 1_555 yes
C(6) C(7) C(12) 119.1(2) 1_555 1_555 yes
C(8) C(7) C(12) 119.3(2) 1_555 1_555 yes
C(7) C(8) C(9) 119.8(2) 1_555 1_555 yes
C(8) C(9) C(10) 120.8(2) 1_555 1_555 yes
C(9) C(10) C(11) 119.7(2) 1_555 1_555 yes
C(10) C(11) C(12) 119.7(2) 1_555 1_555 yes
C(7) C(12) C(11) 120.7(2) 1_555 1_555 yes
O(3) C(13) O(4) 123.9(2) 1_555 1_555 yes
O(3) C(13) C(4) 124.2(2) 1_555 1_555 yes
O(4) C(13) C(4) 111.9(2) 1_555 1_555 yes
O(4) C(14) C(15) 108.5(2) 1_555 1_555 yes
C(14) C(15) C(16) 121.2(2) 1_555 1_555 yes
C(14) C(15) C(20) 120.2(2) 1_555 1_555 yes
C(16) C(15) C(20) 118.6(2) 1_555 1_555 yes
C(15) C(16) C(17) 120.1(2) 1_555 1_555 yes
C(16) C(17) C(18) 120.6(2) 1_555 1_555 yes
C(17) C(18) C(19) 119.9(2) 1_555 1_555 yes
C(18) C(19) C(20) 119.9(2) 1_555 1_555 yes
C(15) C(20) C(19) 120.9(2) 1_555 1_555 yes
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
O(1) C(5) 1.203(3) . yes
O(2) C(5) 1.343(3) . yes
O(2) C(6) 1.457(2) . yes
O(3) C(13) 1.199(3) . yes
O(4) C(13) 1.340(2) . yes
O(4) C(14) 1.467(2) . yes
C(1) C(2) 1.456(3) . yes
C(1) C(3) 1.453(3) 3_557 yes
C(1) C(4) 1.370(3) . yes
C(2) C(3) 1.345(3) . yes
C(4) C(5) 1.498(3) . yes
C(4) C(13) 1.502(3) . yes
C(6) C(7) 1.502(3) . yes
C(7) C(8) 1.385(3) . yes
C(7) C(12) 1.386(3) . yes
C(8) C(9) 1.382(3) . yes
C(9) C(10) 1.381(4) . yes
C(10) C(11) 1.378(4) . yes
C(11) C(12) 1.388(3) . yes
C(14) C(15) 1.494(3) . yes
C(15) C(16) 1.388(3) . yes
C(15) C(20) 1.390(3) . yes
C(16) C(17) 1.387(4) . yes
C(17) C(18) 1.370(4) . yes
C(18) C(19) 1.376(4) . yes
C(19) C(20) 1.381(4) . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) C(10) 3.307(3) 2_646
O(1) C(6) 3.340(3) 3_657
O(2) C(18) 3.365(3) 4_555
O(2) C(9) 3.512(3) 2_656
O(2) C(19) 3.537(3) 4_555
O(3) C(16) 3.324(3) 2_556
O(3) C(10) 3.355(3) 2_656
O(3) C(17) 3.532(3) 4_555
O(4) C(11) 3.361(3) 2_646
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
O(1) C(5) O(2) C(6) -6.1(3) 1_555 1_555 1_555 1_555 yes
O(1) C(5) C(4) C(1) 29.2(3) 1_555 1_555 1_555 1_555 yes
O(1) C(5) C(4) C(13) -156.0(2) 1_555 1_555 1_555 1_555 yes
O(2) C(5) C(4) C(1) -148.9(2) 1_555 1_555 1_555 1_555 yes
O(2) C(5) C(4) C(13) 26.0(2) 1_555 1_555 1_555 1_555 yes
O(2) C(6) C(7) C(8) -46.3(3) 1_555 1_555 1_555 1_555 yes
O(2) C(6) C(7) C(12) 137.4(2) 1_555 1_555 1_555 1_555 yes
O(3) C(13) O(4) C(14) 1.3(3) 1_555 1_555 1_555 1_555 yes
O(3) C(13) C(4) C(1) 51.4(3) 1_555 1_555 1_555 1_555 yes
O(3) C(13) C(4) C(5) -123.5(2) 1_555 1_555 1_555 1_555 yes
O(4) C(13) C(4) C(1) -127.5(2) 1_555 1_555 1_555 1_555 yes
O(4) C(13) C(4) C(5) 57.6(2) 1_555 1_555 1_555 1_555 yes
O(4) C(14) C(15) C(16) 96.7(2) 1_555 1_555 1_555 1_555 yes
O(4) C(14) C(15) C(20) -85.0(3) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(4) C(5) -178.9(2) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(4) C(13) 6.4(3) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(1) C(4) -179.1(2) 1_555 1_555 3_557 3_557 yes
C(3) C(2) C(1) C(4) -179.1(2) 1_555 1_555 1_555 1_555 yes
C(4) C(5) O(2) C(6) 172.0(2) 1_555 1_555 1_555 1_555 yes
C(4) C(13) O(4) C(14) -179.8(2) 1_555 1_555 1_555 1_555 yes
C(5) O(2) C(6) C(7) 125.0(2) 1_555 1_555 1_555 1_555 yes
C(6) C(7) C(8) C(9) -176.2(2) 1_555 1_555 1_555 1_555 yes
C(6) C(7) C(12) C(11) 176.2(2) 1_555 1_555 1_555 1_555 yes
C(7) C(8) C(9) C(10) 0.5(4) 1_555 1_555 1_555 1_555 yes
C(7) C(12) C(11) C(10) -0.3(3) 1_555 1_555 1_555 1_555 yes
C(8) C(7) C(12) C(11) -0.2(3) 1_555 1_555 1_555 1_555 yes
C(8) C(9) C(10) C(11) -1.0(4) 1_555 1_555 1_555 1_555 yes
C(9) C(8) C(7) C(12) 0.1(3) 1_555 1_555 1_555 1_555 yes
C(9) C(10) C(11) C(12) 0.8(4) 1_555 1_555 1_555 1_555 yes
C(13) O(4) C(14) C(15) 174.5(2) 1_555 1_555 1_555 1_555 yes
C(14) C(15) C(16) C(17) 177.8(2) 1_555 1_555 1_555 1_555 yes
C(14) C(15) C(20) C(19) -178.3(2) 1_555 1_555 1_555 1_555 yes
C(15) C(16) C(17) C(18) 0.5(4) 1_555 1_555 1_555 1_555 yes
C(15) C(20) C(19) C(18) 0.4(4) 1_555 1_555 1_555 1_555 yes
C(16) C(15) C(20) C(19) 0.1(3) 1_555 1_555 1_555 1_555 yes
C(16) C(17) C(18) C(19) 0.0(4) 1_555 1_555 1_555 1_555 yes
C(17) C(16) C(15) C(20) -0.5(3) 1_555 1_555 1_555 1_555 yes
C(17) C(18) C(19) C(20) -0.5(4) 1_555 1_555 1_555 1_555 yes
