#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/54/4505445.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_4505445
loop_
_publ_author_name
'Klare, Jennifer E.'
'Tulevski, George S.'
'Nuckolls, Colin'
_publ_section_title
;
 Chemical reactions with upright monolayers of cruciform pi-systems.
;
_journal_issue                   23
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_page_first              10068
_journal_page_last               10072
_journal_paper_doi               10.1021/la0479152
_journal_volume                  20
_journal_year                    2004
_chemical_formula_sum            'C32 H20 N2 O2'
_chemical_formula_weight         464.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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            16
_cell_length_a                   29.530(6)
_cell_length_b                   29.530(6)
_cell_length_c                   10.639(2)
_cell_measurement_temperature    293(2)
_cell_volume                     9277(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  1.5976
_diffrn_reflns_av_sigmaI/netI    0.6899
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            30940
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9594
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3872
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.00070(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.4408
_refine_ls_R_factor_gt           0.1284
_refine_ls_shift/su_max          0.316
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2185
_refine_ls_wR_factor_ref         0.3404
_reflns_number_gt                1194
_reflns_number_total             5307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la0479152si20040821_015040.cif
_cod_data_source_block           cns10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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_original_cell_volume        9278(3)
_cod_original_sg_symbol_H-M      I4(1)/a
_cod_database_code               4505445
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
O1 O 0.47904(18) 1.05870(18) 0.0957(7) 0.0415(18) Uani 1 1 d .
O2 O 0.52517(18) 0.92968(17) 0.4299(7) 0.044(2) Uani 1 1 d .
N1 N 0.5509(2) 1.03344(19) 0.0716(8) 0.0301(19) Uani 1 1 d .
N2 N 0.4536(2) 0.95516(18) 0.4498(7) 0.0259(19) Uani 1 1 d .
C11 C 0.4550(3) 1.0111(2) 0.2727(11) 0.037(3) Uani 1 1 d .
C12 C 0.4859(3) 1.0256(3) 0.1831(11) 0.035(3) Uani 1 1 d .
C13 C 0.5309(2) 1.0104(2) 0.1690(10) 0.028(2) Uani 1 1 d .
C14 C 0.5497(3) 0.9769(3) 0.2480(9) 0.031(2) Uani 1 1 d .
C15 C 0.5188(3) 0.9630(2) 0.3377(10) 0.031(2) Uani 1 1 d .
C16 C 0.4740(2) 0.9776(2) 0.3535(10) 0.030(2) Uani 1 1 d .
C20 C 0.5194(3) 1.0613(3) 0.0285(10) 0.035(3) Uani 1 1 d .
C21 C 0.5246(3) 1.0940(3) -0.0686(11) 0.042(3) Uani 1 1 d .
C22 C 0.4883(3) 1.1220(3) -0.1010(13) 0.063(4) Uani 1 1 d .
H22A H 0.4609 1.1204 -0.0580 0.076 Uiso 1 1 calc R
C23 C 0.4945(5) 1.1526(4) -0.2005(15) 0.082(4) Uani 1 1 d .
H23A H 0.4703 1.1705 -0.2258 0.098 Uiso 1 1 calc R
C24 C 0.5353(5) 1.1568(4) -0.2618(15) 0.088(5) Uani 1 1 d .
H24A H 0.5387 1.1779 -0.3260 0.105 Uiso 1 1 calc R
C25 C 0.5705(4) 1.1297(4) -0.2275(13) 0.074(4) Uani 1 1 d .
H25A H 0.5981 1.1325 -0.2686 0.089 Uiso 1 1 calc R
C26 C 0.5657(3) 1.0979(3) -0.1317(12) 0.051(3) Uani 1 1 d .
H26A H 0.5899 1.0794 -0.1100 0.061 Uiso 1 1 calc R
C31 C 0.4075(2) 1.0291(2) 0.2858(10) 0.037(3) Uani 1 1 d .
C32 C 0.3712(3) 1.0013(3) 0.3318(12) 0.057(4) Uani 1 1 d .
H32A H 0.3767 0.9713 0.3539 0.068 Uiso 1 1 calc R
C33 C 0.3282(3) 1.0193(3) 0.3434(12) 0.052(3) Uani 1 1 d .
H33A H 0.3049 1.0014 0.3752 0.062 Uiso 1 1 calc R
C34 C 0.3191(3) 1.0634(3) 0.3085(12) 0.063(4) Uani 1 1 d .
H34A H 0.2901 1.0751 0.3177 0.076 Uiso 1 1 calc R
C35 C 0.3538(3) 1.0906(3) 0.2592(12) 0.051(3) Uani 1 1 d .
H35A H 0.3475 1.1201 0.2342 0.061 Uiso 1 1 calc R
C36 C 0.3981(3) 1.0735(3) 0.2472(11) 0.045(3) Uani 1 1 d .
H36A H 0.4210 1.0916 0.2140 0.054 Uiso 1 1 calc R
C40 C 0.4851(3) 0.9279(3) 0.4930(10) 0.038(3) Uani 1 1 d .
C41 C 0.4813(3) 0.8950(3) 0.5942(10) 0.039(3) Uani 1 1 d .
C42 C 0.5148(3) 0.8611(3) 0.6116(11) 0.045(3) Uani 1 1 d .
H42A H 0.5397 0.8596 0.5581 0.054 Uiso 1 1 calc R
C43 C 0.5102(3) 0.8305(3) 0.7080(12) 0.057(3) Uani 1 1 d .
H43A H 0.5317 0.8078 0.7180 0.069 Uiso 1 1 calc R
C44 C 0.4743(4) 0.8329(3) 0.7902(12) 0.062(3) Uani 1 1 d .
H44A H 0.4723 0.8125 0.8565 0.075 Uiso 1 1 calc R
C45 C 0.4410(3) 0.8658(3) 0.7742(12) 0.050(3) Uani 1 1 d .
H45A H 0.4160 0.8666 0.8276 0.061 Uiso 1 1 calc R
C46 C 0.4449(3) 0.8965(3) 0.6808(11) 0.040(3) Uani 1 1 d .
H46A H 0.4233 0.9192 0.6732 0.048 Uiso 1 1 calc R
C51 C 0.5974(2) 0.9607(2) 0.2357(9) 0.026(2) Uani 1 1 d .
C52 C 0.6172(3) 0.9580(3) 0.1206(12) 0.046(3) Uani 1 1 d .
H52A H 0.6005 0.9657 0.0497 0.056 Uiso 1 1 calc R
C53 C 0.6623(3) 0.9436(3) 0.1064(13) 0.057(3) Uani 1 1 d .
H53A H 0.6752 0.9426 0.0266 0.069 Uiso 1 1 calc R
C54 C 0.6873(3) 0.9311(3) 0.2079(14) 0.057(3) Uani 1 1 d .
H54A H 0.7169 0.9207 0.1993 0.068 Uiso 1 1 calc R
C55 C 0.6677(3) 0.9345(3) 0.3208(14) 0.069(4) Uani 1 1 d .
H55A H 0.6845 0.9263 0.3911 0.083 Uiso 1 1 calc R
C56 C 0.6238(3) 0.9495(3) 0.3388(12) 0.055(3) Uani 1 1 d .
H56A H 0.6120 0.9520 0.4196 0.066 Uiso 1 1 calc R
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'
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
C12 O1 C20 105.2(6)
C40 O2 C15 104.8(7)
C20 N1 C13 105.6(6)
C40 N2 C16 104.3(7)
C12 C11 C16 111.6(7)
C12 C11 C31 124.6(8)
C16 C11 C31 123.7(8)
O1 C12 C11 126.2(7)
O1 C12 C13 107.2(8)
C11 C12 C13 126.6(8)
N1 C13 C12 109.1(7)
N1 C13 C14 128.9(7)
C12 C13 C14 122.0(8)
C15 C14 C13 111.0(7)
C15 C14 C51 126.0(8)
C13 C14 C51 122.9(8)
C14 C15 O2 127.1(7)
C14 C15 C16 127.9(8)
O2 C15 C16 105.0(8)
N2 C16 C15 111.0(7)
N2 C16 C11 128.1(7)
C15 C16 C11 120.8(8)
N1 C20 O1 112.9(8)
N1 C20 C21 126.7(8)
O1 C20 C21 120.3(7)
C22 C21 C26 120.1(10)
C22 C21 C20 119.8(9)
C26 C21 C20 120.1(8)
C23 C22 C21 117.8(11)
C22 C23 C24 122.1(12)
C25 C24 C23 119.2(12)
C24 C25 C26 120.9(11)
C25 C26 C21 119.9(10)
C36 C31 C32 119.1(7)
C36 C31 C11 119.2(7)
C32 C31 C11 121.7(7)
C33 C32 C31 119.8(7)
C34 C33 C32 121.0(8)
C33 C34 C35 120.0(8)
C36 C35 C34 120.5(8)
C31 C36 C35 119.5(7)
N2 C40 O2 114.8(8)
N2 C40 C41 127.9(8)
O2 C40 C41 117.2(8)
C46 C41 C42 117.8(9)
C46 C41 C40 121.2(8)
C42 C41 C40 121.0(9)
C43 C42 C41 119.4(10)
C44 C43 C42 121.2(10)
C43 C44 C45 120.2(11)
C46 C45 C44 119.8(10)
C45 C46 C41 121.5(9)
C52 C51 C56 117.3(8)
C52 C51 C14 120.2(9)
C56 C51 C14 122.5(9)
C51 C52 C53 121.4(11)
C54 C53 C52 120.7(12)
C55 C54 C53 117.3(10)
C54 C55 C56 123.7(12)
C55 C56 C51 119.6(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.366(10)
O1 C20 1.391(10)
O2 C40 1.361(9)
O2 C15 1.401(10)
N1 C20 1.325(10)
N1 C13 1.373(11)
N2 C40 1.314(10)
N2 C16 1.361(11)
C11 C12 1.387(13)
C11 C16 1.426(12)
C11 C31 1.505(10)
C12 C13 1.410(10)
C13 C14 1.412(12)
C14 C15 1.383(12)
C14 C51 1.493(10)
C15 C16 1.402(10)
C20 C21 1.422(13)
C21 C22 1.396(11)
C21 C26 1.392(12)
C22 C23 1.403(17)
C23 C24 1.375(16)
C24 C25 1.362(15)
C25 C26 1.393(15)
C31 C36 1.403(10)
C31 C32 1.435(11)
C32 C33 1.384(10)
C33 C34 1.381(11)
C34 C35 1.402(12)
C35 C36 1.408(10)
C40 C41 1.456(13)
C41 C46 1.417(13)
C41 C42 1.418(10)
C42 C43 1.373(14)
C43 C44 1.376(14)
C44 C45 1.393(12)
C45 C46 1.350(14)
C51 C52 1.359(13)
C51 C56 1.385(14)
C52 C53 1.408(11)
C53 C54 1.360(15)
C54 C55 1.336(17)
C55 C56 1.385(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661516
