#------------------------------------------------------------------------------
#$Date: 2021-10-23 07:42:03 +0300 (Sat, 23 Oct 2021) $
#$Revision: 270064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/00/4020004.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_4020004
loop_
_publ_author_name
'Blakemore, Paul R.'
'Kilner, Colin'
'Milicevic, Selena D.'
_publ_section_title
;
 Harnessing Anionic Rearrangements on the Benzenoid Ring of Quinoline
 for the Synthesis of 6,6'-Disubstituted 7,7'-Dihydroxy-8,8'-biquinolyls
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   1
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              373
_journal_page_last               376
_journal_paper_doi               10.1021/jo048258l
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         'C28 H28 I2 N4 O4'
_chemical_formula_sum            'C28 H28 I2 N4 O4'
_chemical_formula_weight         738.34
_chemical_name_systematic
;
7,7'-bis(diethylaminocarbonyloxy)-6,6'-diiodo-8,8'-biquinolyl
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.7820(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3233(2)
_cell_length_b                   18.2087(4)
_cell_length_c                   13.2098(3)
_cell_measurement_reflns_used    16214
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2890.71(10)
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'phi-omega scans'
_diffrn_radiation_detector       'CCD plate'
_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  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30034
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_T_max  0.9166
_exptl_absorpt_correction_T_min  0.5862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Using multiple and symmetry-related data
 measurements via the program SORTAV.  See
 R.H. Blessing, Acta Cryst (1995), A51, 33-38.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.5818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                4163
_reflns_number_total             5677
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4020004
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
I10' I 0.52693(2) 0.180493(14) 0.74336(2) 0.03899(11) Uani 1 1 d . . .
I10 I -0.11827(2) 0.242301(17) 0.85441(3) 0.05610(12) Uani 1 1 d . . .
N4' N 0.3084(2) 0.05940(16) 1.0956(2) 0.0306(7) Uani 1 1 d . . .
C8' C 0.4772(3) 0.08701(19) 1.0342(3) 0.0289(8) Uani 1 1 d . . .
O11' O 0.2731(2) 0.15393(12) 0.75221(18) 0.0299(6) Uani 1 1 d . . .
N4 N 0.1877(3) -0.03648(16) 0.9055(2) 0.0318(7) Uani 1 1 d . . .
C10' C 0.4571(3) 0.13655(19) 0.8616(3) 0.0305(9) Uani 1 1 d . . .
C5' C 0.3732(3) 0.0404(2) 1.1841(3) 0.0365(9) Uani 1 1 d . . .
H5' H 0.3386 0.0259 1.2384 0.044 Uiso 1 1 calc R . .
C10 C -0.0180(3) 0.1480(2) 0.8722(3) 0.0342(9) Uani 1 1 d . . .
C2' C 0.2906(3) 0.10284(18) 0.9213(3) 0.0257(8) Uani 1 1 d . . .
C5 C 0.1397(3) -0.1013(2) 0.8994(3) 0.0363(9) Uani 1 1 d . . .
H5 H 0.1868 -0.1432 0.9078 0.044 Uiso 1 1 calc R . .
C9' C 0.5242(3) 0.11441(19) 0.9531(3) 0.0308(8) Uani 1 1 d . . .
H9' H 0.6027 0.1174 0.9624 0.037 Uiso 1 1 calc R . .
C12' C 0.2497(3) 0.1032(2) 0.6723(3) 0.0329(9) Uani 1 1 d . . .
C2 C 0.1674(3) 0.09490(18) 0.9028(2) 0.0245(8) Uani 1 1 d . . .
C8 C 0.0009(3) 0.0167(2) 0.8742(3) 0.0313(8) Uani 1 1 d . . .
C7' C 0.5422(3) 0.0637(2) 1.1304(3) 0.0335(9) Uani 1 1 d . . .
H7' H 0.6211 0.0645 1.1430 0.040 Uiso 1 1 calc R . .
C3' C 0.3595(3) 0.08274(18) 1.0189(3) 0.0268(8) Uani 1 1 d . . .
O12' O 0.2841(2) 0.04087(15) 0.6829(2) 0.0462(7) Uani 1 1 d . . .
C6' C 0.4899(3) 0.0398(2) 1.2050(3) 0.0363(9) Uani 1 1 d . . .
H6' H 0.5318 0.0231 1.2702 0.044 Uiso 1 1 calc R . .
C1 C 0.0990(3) 0.15523(19) 0.8925(3) 0.0287(8) Uani 1 1 d . . .
C6 C 0.0248(3) -0.1136(2) 0.8814(3) 0.0385(10) Uani 1 1 d . . .
H6 H -0.0039 -0.1622 0.8786 0.046 Uiso 1 1 calc R . .
C3 C 0.1182(3) 0.02340(19) 0.8931(3) 0.0274(8) Uani 1 1 d . . .
N13' N 0.1864(3) 0.13327(18) 0.5867(2) 0.0418(8) Uani 1 1 d . . .
C1' C 0.3407(3) 0.12928(18) 0.8453(3) 0.0271(8) Uani 1 1 d . . .
O11 O 0.1480(2) 0.22427(12) 0.89374(18) 0.0301(6) Uani 1 1 d . . .
O12 O 0.1305(2) 0.24524(14) 1.0598(2) 0.0422(7) Uani 1 1 d . . .
N13 N 0.1969(3) 0.33342(16) 0.9659(2) 0.0338(8) Uani 1 1 d . . .
C12 C 0.1565(3) 0.2675(2) 0.9819(3) 0.0341(9) Uani 1 1 d . . .
C9 C -0.0651(3) 0.0810(2) 0.8626(3) 0.0350(9) Uani 1 1 d . . .
H9 H -0.1439 0.0767 0.8479 0.042 Uiso 1 1 calc R . .
C14 C 0.2213(3) 0.3570(2) 0.8664(3) 0.0368(9) Uani 1 1 d . . .
H14A H 0.2105 0.4107 0.8586 0.044 Uiso 1 1 calc R . .
H14B H 0.1688 0.3328 0.8085 0.044 Uiso 1 1 calc R . .
C7 C -0.0447(3) -0.0549(2) 0.8680(3) 0.0377(10) Uani 1 1 d . . .
H7 H -0.1230 -0.0618 0.8546 0.045 Uiso 1 1 calc R . .
C16' C 0.1445(4) 0.2090(2) 0.5824(3) 0.0485(11) Uani 1 1 d . . .
H16C H 0.1306 0.2265 0.5097 0.058 Uiso 1 1 calc R . .
H16D H 0.2025 0.2408 0.6245 0.058 Uiso 1 1 calc R . .
C16 C 0.2095(4) 0.3876(2) 1.0498(3) 0.0475(11) Uani 1 1 d . . .
H16A H 0.2789 0.4159 1.0531 0.057 Uiso 1 1 calc R . .
H16B H 0.2161 0.3618 1.1168 0.057 Uiso 1 1 calc R . .
C15 C 0.3389(4) 0.3379(3) 0.8609(4) 0.0583(13) Uani 1 1 d . . .
H15A H 0.3910 0.3610 0.9190 0.087 Uiso 1 1 calc R . .
H15B H 0.3536 0.3557 0.7952 0.087 Uiso 1 1 calc R . .
H15C H 0.3486 0.2845 0.8650 0.087 Uiso 1 1 calc R . .
C14' C 0.1444(5) 0.0835(3) 0.4983(3) 0.0649(15) Uani 1 1 d . . .
H14C H 0.0625 0.0883 0.4767 0.078 Uiso 1 1 calc R . .
H14D H 0.1616 0.0321 0.5206 0.078 Uiso 1 1 calc R . .
C17' C 0.0392(4) 0.2168(3) 0.6212(3) 0.0552(13) Uani 1 1 d . . .
H17A H -0.0178 0.1840 0.5819 0.083 Uiso 1 1 calc R . .
H17B H 0.0130 0.2677 0.6121 0.083 Uiso 1 1 calc R . .
H17C H 0.0539 0.2038 0.6950 0.083 Uiso 1 1 calc R . .
C17 C 0.1126(5) 0.4397(2) 1.0338(4) 0.0617(14) Uani 1 1 d . . .
H17D H 0.1124 0.4704 0.9728 0.093 Uiso 1 1 calc R . .
H17E H 0.1192 0.4710 1.0952 0.093 Uiso 1 1 calc R . .
H17F H 0.0431 0.4116 1.0230 0.093 Uiso 1 1 calc R . .
C15' C 0.1943(6) 0.0999(3) 0.4086(4) 0.098(2) Uani 1 1 d . . .
H15D H 0.1753 0.1502 0.3848 0.147 Uiso 1 1 calc R . .
H15E H 0.1653 0.0654 0.3522 0.147 Uiso 1 1 calc R . .
H15F H 0.2754 0.0950 0.4296 0.147 Uiso 1 1 calc R . .
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2021-10-23T07:30:00+03:00
'Updated bibliographic information.'
