#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:29:33 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179633 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/97/4509743.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509743
loop_
_publ_author_name
'Santra, Ramkinkar'
'Biradha, Kumar'
_publ_section_title
;
 Two-Dimensional Organic Brick-Wall Layers as Hosts for the Inclusion and
 Study of Aromatics Ensembles: Acid−Pyridine and
 Acid−Carbonyl Synthons for Multicomponent Materials
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4969
_journal_paper_doi               10.1021/cg900759e
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C82 H66 N4 O16'
_chemical_formula_weight         1363.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 122.438(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.4878(16)
_cell_length_b                   24.9242(18)
_cell_length_c                   14.3780(10)
_cell_measurement_reflns_used    6345
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      1.35
_cell_volume                     6801.3(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker CCD APEX-2'
_diffrn_measurement_method       hemisphere
_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  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            41717
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'deep yellow'
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             2856
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00022(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.744
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         6345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.744
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1245P)²+20.0262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.2137
_reflns_number_gt                3459
_reflns_number_total             6345
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg900759esup1.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4509743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O11 O 0.21031(12) -0.04855(9) 0.0752(2) 0.0780(8) Uani 1 1 d .
O12 O 0.31073(13) -0.09214(9) 0.1760(2) 0.0758(8) Uani 1 1 d .
H12O H 0.2868(16) -0.1210(13) 0.153(2) 0.050 Uiso 1 1 d .
O13 O 0.52639(13) -0.00943(10) 0.4053(3) 0.0968(12) Uani 1 1 d .
H13O H 0.5589(18) -0.0123(15) 0.438(3) 0.050 Uiso 1 1 d .
O14 O 0.54260(13) 0.07847(10) 0.4266(3) 0.0948(10) Uani 1 1 d .
O15 O 0.33172(15) 0.19036(10) 0.2071(3) 0.0801(9) Uani 1 1 d .
H15O H 0.3133(17) 0.2171(14) 0.196(3) 0.050 Uiso 1 1 d .
O16 O 0.22450(14) 0.15608(10) 0.1010(2) 0.0782(8) Uani 1 1 d .
C11 C 0.31541(15) 0.00113(11) 0.1841(2) 0.0448(7) Uani 1 1 d .
C12 C 0.38733(15) -0.00238(11) 0.2600(3) 0.0509(8) Uani 1 1 d .
H12 H 0.4088 -0.0359 0.2820 0.061 Uiso 1 1 calc R
C13 C 0.42752(15) 0.04376(11) 0.3034(3) 0.0512(8) Uani 1 1 d .
C14 C 0.39498(16) 0.09342(12) 0.2714(3) 0.0512(8) Uani 1 1 d .
H14 H 0.4217 0.1245 0.3007 0.061 Uiso 1 1 calc R
C15 C 0.32321(15) 0.09730(11) 0.1962(3) 0.0474(7) Uani 1 1 d .
C16 C 0.28354(15) 0.05102(11) 0.1526(3) 0.0465(7) Uani 1 1 d .
H16 H 0.2353 0.0535 0.1018 0.056 Uiso 1 1 calc R
C17 C 0.27310(16) -0.04908(12) 0.1388(3) 0.0503(8) Uani 1 1 d .
C18 C 0.50444(17) 0.04057(13) 0.3848(3) 0.0650(10) Uani 1 1 d .
C19 C 0.28756(19) 0.15089(13) 0.1622(3) 0.0571(8) Uani 1 1 d .
O11A O 0.15484(12) 0.54672(8) 0.0389(2) 0.0779(8) Uani 1 1 d .
N1A N 0.28398(18) 0.28727(11) 0.1678(3) 0.0686(8) Uani 1 1 d .
C11A C 0.21872(15) 0.54769(11) 0.1024(3) 0.0488(7) Uani 1 1 d .
C12A C 0.26004(15) 0.49654(11) 0.1436(2) 0.0468(7) Uani 1 1 d .
C13A C 0.33882(17) 0.50029(13) 0.2151(3) 0.0622(9) Uani 1 1 d .
H13A H 0.3592 0.4704 0.1982 0.075 Uiso 1 1 calc .
H13B H 0.3531 0.4970 0.2916 0.075 Uiso 1 1 calc .
C14A C 0.36804(17) 0.55204(13) 0.2008(3) 0.0610(9) Uani 1 1 d .
H14A H 0.4185 0.5531 0.2534 0.073 Uiso 1 1 calc .
H14B H 0.3598 0.5532 0.1273 0.073 Uiso 1 1 calc .
C15A C 0.33454(16) 0.60029(12) 0.2176(3) 0.0574(9) Uani 1 1 d .
H15A H 0.3461 0.6006 0.2930 0.069 Uiso 1 1 calc .
H15B H 0.3538 0.6326 0.2062 0.069 Uiso 1 1 calc .
C16A C 0.25588(14) 0.60042(11) 0.1404(2) 0.0458(7) Uani 1 1 d .
N2A N 0.25889(14) 0.81161(10) 0.1296(2) 0.0557(7) Uani 1 1 d .
C21A C 0.3259(2) 0.32421(13) 0.2384(3) 0.0651(10) Uani 1 1 d .
H21A H 0.3689 0.3133 0.2992 0.078 Uiso 1 1 calc R
C22A C 0.30960(18) 0.37768(12) 0.2272(3) 0.0582(9) Uani 1 1 d .
H22A H 0.3407 0.4021 0.2799 0.070 Uiso 1 1 calc R
C23A C 0.24646(16) 0.39526(11) 0.1367(3) 0.0479(7) Uani 1 1 d .
C24A C 0.2013(2) 0.35626(13) 0.0642(3) 0.0649(10) Uani 1 1 d .
H24A H 0.1574 0.3658 0.0039 0.078 Uiso 1 1 calc R
C25A C 0.2221(2) 0.30335(14) 0.0822(3) 0.0760(11) Uani 1 1 d .
H25A H 0.1915 0.2777 0.0325 0.091 Uiso 1 1 calc R
C26A C 0.22266(16) 0.45101(11) 0.1120(3) 0.0494(8) Uani 1 1 d .
H26A H 0.1741 0.4555 0.0674 0.059 Uiso 1 1 calc R
C31A C 0.30472(17) 0.77808(13) 0.2062(3) 0.0586(9) Uani 1 1 d .
H31A H 0.3466 0.7921 0.2646 0.070 Uiso 1 1 calc R
C32A C 0.29392(16) 0.72379(12) 0.2043(3) 0.0541(8) Uani 1 1 d .
H32A H 0.3273 0.7022 0.2612 0.065 Uiso 1 1 calc R
C33A C 0.23278(14) 0.70135(11) 0.1166(3) 0.0444(7) Uani 1 1 d .
C34A C 0.18402(15) 0.73723(11) 0.0376(3) 0.0509(8) Uani 1 1 d .
H34A H 0.1414 0.7246 -0.0214 0.061 Uiso 1 1 calc R
C35A C 0.19897(17) 0.79098(12) 0.0470(3) 0.0562(8) Uani 1 1 d .
H35A H 0.1658 0.8141 -0.0067 0.067 Uiso 1 1 calc R
C36A C 0.21447(15) 0.64425(11) 0.0996(3) 0.0468(7) Uani 1 1 d .
H36A H 0.1666 0.6371 0.0532 0.056 Uiso 1 1 calc R
O101 O 0.0809(3) -0.0824(3) 0.0097(5) 0.0975(18) Uani 0.50 1 d P
C101 C 0.0412(2) -0.0410(2) -0.0003(4) 0.0898(13) Uani 1 1 d .
C102 C 0.0512(2) 0.0103(2) -0.0210(4) 0.0919(14) Uani 1 1 d .
H102 H 0.0860 0.0177 -0.0353 0.110 Uiso 1 1 calc R
C103 C -0.0097(3) -0.0520(2) 0.0210(4) 0.0984(15) Uani 1 1 d .
H103 H -0.0167 -0.0870 0.0355 0.118 Uiso 1 1 calc R
O201 O 0.1129(4) 0.1161(3) -0.0796(7) 0.121(2) Uani 0.50 1 d P
C201 C 0.0571(3) 0.1555(4) -0.1629(6) 0.145(3) Uani 1 1 d .
C202 C 0.0580(8) 0.2076(4) -0.1620(13) 0.247(7) Uani 1 1 d .
H202 H 0.0970 0.2245 -0.1033 0.297 Uiso 1 1 calc R
C203 C 0.0000 0.2427(7) -0.2500 0.264(13) Uani 1 2 d S
H203 H 0.0000 0.2800 -0.2500 0.317 Uiso 1 2 calc SR
C204 C 0.0000 0.1300(5) -0.2500 0.142(3) Uani 1 2 d S
H204 H 0.0000 0.0927 -0.2500 0.170 Uiso 1 2 calc SR
C300 C -0.00099(15) 0.27036(14) 0.2969(3) 0.0561(8) Uani 1 1 d .
C301 C -0.0065(3) 0.2455(4) 0.4703(6) 0.132(2) Uani 1 1 d .
C302 C -0.0058(3) 0.2999(4) 0.4711(5) 0.124(2) Uani 1 1 d .
C303 C -0.0013(3) 0.3126(4) 0.3534(9) 0.148(4) Uani 1 1 d .
C304 C 0.0000 0.3734(2) 0.2500 0.0815(18) Uani 1 2 d S
C305 C 0.0000 0.1676(3) 0.2500 0.108(4) Uani 1 2 d S
C306 C -0.0051(4) 0.1830(4) 0.3307(12) 0.186(6) Uani 1 1 d .
C307 C -0.0045(5) 0.3430(6) 0.4212(9) 0.099(3) Uani 0.50 1 d P
C308 C -0.0023(3) 0.2260(4) 0.3481(6) 0.139(3) Uani 1 1 d .
C309 C -0.0011(6) 0.2020(8) 0.4338(11) 0.116(5) Uani 0.50 1 d P
C310 C -0.0031(4) 0.3545(4) 0.3296(9) 0.151(3) Uani 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 C11 C16 119.7(3) . .
C12 C11 C17 119.5(3) . .
C16 C11 C17 120.9(3) . .
C11 C12 C13 120.4(3) . .
C14 C13 C12 119.4(3) . .
C14 C13 C18 119.7(3) . .
C12 C13 C18 120.9(3) . .
C15 C14 C13 120.6(3) . .
C14 C15 C16 119.6(3) . .
C14 C15 C19 120.9(3) . .
C16 C15 C19 119.5(3) . .
C11 C16 C15 120.3(3) . .
O11 C17 O12 124.4(3) . .
O11 C17 C11 122.4(3) . .
O12 C17 C11 113.2(3) . .
O14 C18 O13 123.6(3) . .
O14 C18 C13 124.9(3) . .
O13 C18 C13 111.5(3) . .
O16 C19 O15 124.5(3) . .
O16 C19 C15 123.1(3) . .
O15 C19 C15 112.4(3) . .
C21A N1A C25A 117.5(3) . .
O11A C11A C16A 119.6(3) . .
O11A C11A C12A 120.6(3) . .
C16A C11A C12A 119.8(2) . .
C26A C12A C13A 125.5(3) . .
C26A C12A C11A 116.3(3) . .
C13A C12A C11A 118.1(3) . .
C12A C13A C14A 113.6(3) . .
C15A C14A C13A 111.6(3) . .
C16A C15A C14A 112.0(3) . .
C36A C16A C15A 126.0(3) . .
C36A C16A C11A 115.7(2) . .
C15A C16A C11A 118.3(2) . .
C31A N2A C35A 117.5(3) . .
N1A C21A C22A 123.6(3) . .
C21A C22A C23A 119.6(3) . .
C22A C23A C24A 116.9(3) . .
C22A C23A C26A 125.9(3) . .
C24A C23A C26A 117.2(3) . .
C25A C24A C23A 119.5(3) . .
N1A C25A C24A 122.9(4) . .
C12A C26A C23A 129.9(3) . .
N2A C31A C32A 123.7(3) . .
C31A C32A C33A 119.6(3) . .
C32A C33A C34A 116.3(3) . .
C32A C33A C36A 126.5(3) . .
C34A C33A C36A 117.2(3) . .
C35A C34A C33A 120.1(3) . .
N2A C35A C34A 122.9(3) . .
C16A C36A C33A 130.4(3) . .
O101 C101 C103 114.6(6) . .
O101 C101 C102 125.3(5) . .
C103 C101 C102 119.9(5) . .
C101 C102 C103 120.8(5) . 5
C101 C103 C102 119.3(5) . 5
C202 C201 C204 118.1(11) . .
C202 C201 O201 129.0(10) . .
C204 C201 O201 112.9(9) . .
C201 C202 C203 124.6(15) . .
C202 C203 C202 109.4(15) 2_554 .
C201 C204 C201 125.2(13) . 2_554
C303 C300 C300 127.8(6) . 2
C303 C300 C308 108.0(8) . .
C300 C300 C308 124.3(5) 2 .
C309 C301 C302 151.1(9) . .
C309 C301 C308 46.3(6) . .
C302 C301 C308 105.1(6) . .
C307 C302 C301 145.6(8) . .
C307 C302 C303 45.4(5) . .
C301 C302 C303 100.2(6) . .
C310 C303 C307 70.3(10) . .
C310 C303 C300 125.1(15) . .
C307 C303 C300 164.3(14) . .
C310 C303 C302 117.3(11) . .
C307 C303 C302 47.0(9) . .
C300 C303 C302 117.5(8) . .
C310 C303 C308 161.1(13) . .
C307 C303 C308 128.4(12) . .
C300 C303 C308 36.1(4) . .
C302 C303 C308 81.4(6) . .
C310 C304 C310 136.5(12) . 2
C306 C305 C306 145.2(13) 2 .
C305 C306 C308 118.5(16) . .
C305 C306 C309 172.8(8) . .
C308 C306 C309 60.2(10) . .
C303 C307 C302 87.6(12) . .
C303 C307 C310 48.9(6) . .
C302 C307 C310 136.4(12) . .
C306 C308 C309 75.3(11) . .
C306 C308 C300 134.4(14) . .
C309 C308 C300 150.4(15) . .
C306 C308 C301 116.2(11) . .
C309 C308 C301 41.3(10) . .
C300 C308 C301 109.2(8) . .
C306 C308 C303 170.1(13) . .
C309 C308 C303 114.4(13) . .
C300 C308 C303 36.0(5) . .
C301 C308 C303 73.3(6) . .
C301 C309 C308 92.3(13) . .
C301 C309 C306 136.3(12) . .
C308 C309 C306 44.5(6) . .
C303 C310 C304 128.7(15) . .
C303 C310 C307 60.8(9) . .
C304 C310 C307 170.2(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C17 1.202(4) .
O12 C17 1.292(4) .
O13 C18 1.314(4) .
O14 C18 1.199(4) .
O15 C19 1.297(4) .
O16 C19 1.210(4) .
C11 C12 1.386(4) .
C11 C16 1.384(4) .
C11 C17 1.494(4) .
C12 C13 1.387(4) .
C13 C14 1.385(4) .
C13 C18 1.482(4) .
C14 C15 1.382(4) .
C15 C16 1.386(4) .
C15 C19 1.498(4) .
O11A C11A 1.221(3) .
N1A C21A 1.319(5) .
N1A C25A 1.333(5) .
C11A C16A 1.495(4) .
C11A C12A 1.500(4) .
C12A C26A 1.338(4) .
C12A C13A 1.500(4) .
C13A C14A 1.510(5) .
C14A C15A 1.506(5) .
C15A C16A 1.502(4) .
C16A C36A 1.349(4) .
N2A C31A 1.325(4) .
N2A C35A 1.332(4) .
C21A C22A 1.369(4) .
C22A C23A 1.385(4) .
C23A C24A 1.388(5) .
C23A C26A 1.463(4) .
C24A C25A 1.376(5) .
C31A C32A 1.372(4) .
C32A C33A 1.390(4) .
C33A C34A 1.398(4) .
C33A C36A 1.465(4) .
C34A C35A 1.370(4) .
O101 C101 1.322(7) .
C101 C103 1.361(7) .
C101 C102 1.356(7) .
C102 C103 1.398(7) 5
C103 C102 1.398(7) 5
O201 C201 1.536(10) .
C201 C202 1.299(11) .
C201 C204 1.376(8) .
C202 C203 1.516(13) .
C203 C202 1.516(13) 2_554
C204 C201 1.376(8) 2_554
C300 C303 1.333(8) .
C300 C300 1.372(7) 2
C300 C308 1.337(7) .
C301 C309 1.239(19) .
C301 C302 1.355(10) .
C301 C308 1.874(13) .
C302 C307 1.301(15) .
C302 C303 1.777(13) .
C303 C310 1.093(10) .
C303 C307 1.267(11) .
C303 C308 2.159(13) .
C304 C310 1.273(11) .
C304 C310 1.273(11) 2
C305 C306 1.284(15) 2
C305 C306 1.284(15) .
C306 C308 1.096(12) .
C306 C309 1.512(18) .
C307 C310 1.366(14) .
C308 C309 1.357(13) .
