#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:29:33 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179633 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/97/4509744.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_4509744
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 O18'
_chemical_formula_weight         1395.39
_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                 122.680(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.4015(13)
_cell_length_b                   24.8681(14)
_cell_length_c                   14.4804(8)
_cell_measurement_reflns_used    6531
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      1.36
_cell_volume                     6789.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42614
_diffrn_reflns_theta_full        25.80
_diffrn_reflns_theta_max         25.80
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'deep yellow'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             2920
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0959P)²+8.3033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1965
_reflns_number_gt                3466
_reflns_number_total             6531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg900759esup1.cif
_cod_data_source_block           11
_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               4509744
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
O1 O 0.19085(12) -0.59069(8) 0.8257(2) 0.0713(8) Uani 1 1 d .
H1O H 0.2176(15) -0.6236(12) 0.853(2) 0.050 Uiso 1 1 d .
O2 O 0.28986(11) -0.54608(9) 0.9326(2) 0.0725(8) Uani 1 1 d .
O3 O 0.27544(13) -0.34197(9) 0.9027(2) 0.0710(7) Uani 1 1 d .
O4 O 0.16828(13) -0.30710(8) 0.7943(2) 0.0764(8) Uani 1 1 d .
H4O H 0.1968(15) -0.2677(12) 0.819(2) 0.050 Uiso 1 1 d .
O5 O -0.02675(13) -0.50882(9) 0.5933(3) 0.0977(12) Uani 1 1 d .
H5O H -0.0668(18) -0.5126(12) 0.550(3) 0.050 Uiso 1 1 d .
O6 O -0.04345(12) -0.42083(9) 0.5706(3) 0.0908(10) Uani 1 1 d .
C1 C 0.18454(14) -0.49729(10) 0.8188(2) 0.0417(7) Uani 1 1 d .
C2 C 0.21649(15) -0.44733(10) 0.8511(3) 0.0428(7) Uani 1 1 d .
H2 H 0.2649 -0.4449 0.9031 0.051 Uiso 1 1 calc R
C3 C 0.17663(15) -0.40084(10) 0.8064(3) 0.0441(7) Uani 1 1 d .
C4 C 0.10441(15) -0.40497(11) 0.7293(3) 0.0481(8) Uani 1 1 d .
H4 H 0.0774 -0.3740 0.6995 0.058 Uiso 1 1 calc R
C5 C 0.07215(15) -0.45483(11) 0.6964(3) 0.0508(8) Uani 1 1 d .
C6 C 0.11293(15) -0.50082(10) 0.7416(3) 0.0474(8) Uani 1 1 d .
H6 H 0.0916 -0.5344 0.7195 0.057 Uiso 1 1 calc R
C7 C 0.22712(15) -0.54735(11) 0.8651(3) 0.0456(8) Uani 1 1 d .
C8 C 0.21186(18) -0.34680(12) 0.8397(3) 0.0524(8) Uani 1 1 d .
C9 C -0.00484(16) -0.45828(12) 0.6139(3) 0.0647(11) Uani 1 1 d .
O11 O 0.34532(11) 0.04798(8) 0.9583(2) 0.0767(9) Uani 1 1 d .
C11 C 0.28121(15) 0.04919(10) 0.8946(3) 0.0448(8) Uani 1 1 d .
C12 C 0.23918(14) -0.00158(10) 0.8532(2) 0.0406(7) Uani 1 1 d .
C13 C 0.16028(16) 0.00221(12) 0.7813(3) 0.0549(9) Uani 1 1 d .
H13A H 0.1397 -0.0275 0.7981 0.066 Uiso 1 1 calc .
H13B H 0.1462 -0.0015 0.7055 0.066 Uiso 1 1 calc .
C14 C 0.13058(16) 0.05387(12) 0.7935(3) 0.0542(9) Uani 1 1 d .
H14A H 0.1378 0.0552 0.8658 0.065 Uiso 1 1 calc .
H14B H 0.0799 0.0550 0.7395 0.065 Uiso 1 1 calc .
C15 C 0.16518(15) 0.10191(11) 0.7784(3) 0.0534(9) Uani 1 1 d .
H15A H 0.1542 0.1022 0.7038 0.064 Uiso 1 1 calc .
H15B H 0.1456 0.1344 0.7889 0.064 Uiso 1 1 calc .
C16 C 0.24400(14) 0.10233(10) 0.8563(2) 0.0421(7) Uani 1 1 d .
C17 C 0.28543(15) 0.14585(11) 0.8987(3) 0.0444(8) Uani 1 1 d .
H17 H 0.3335 0.1384 0.9458 0.053 Uiso 1 1 calc R
C18 C 0.27669(15) -0.04731(10) 0.8854(3) 0.0447(8) Uani 1 1 d .
H18 H 0.3256 -0.0428 0.9301 0.054 Uiso 1 1 calc R
N21 N 0.24254(13) 0.31379(9) 0.8725(2) 0.0513(7) Uani 1 1 d .
C21 C 0.19578(16) 0.28052(12) 0.7947(3) 0.0534(9) Uani 1 1 d .
H21 H 0.1538 0.2949 0.7366 0.064 Uiso 1 1 calc R
C22 C 0.20634(16) 0.22625(11) 0.7959(3) 0.0513(8) Uani 1 1 d .
H22 H 0.1727 0.2048 0.7386 0.062 Uiso 1 1 calc R
C23 C 0.26768(14) 0.20317(10) 0.8832(2) 0.0413(7) Uani 1 1 d .
C24 C 0.31654(15) 0.23879(11) 0.9621(3) 0.0470(8) Uani 1 1 d .
H24 H 0.3592 0.2258 1.0209 0.056 Uiso 1 1 calc R
C25 C 0.30244(16) 0.29268(11) 0.9541(3) 0.0506(8) Uani 1 1 d .
H25 H 0.3362 0.3155 1.0081 0.061 Uiso 1 1 calc R
N31 N 0.21547(15) -0.21140(10) 0.8315(3) 0.0583(8) Uani 1 1 d .
C31 C 0.17263(18) -0.17475(12) 0.7601(3) 0.0552(9) Uani 1 1 d .
H31 H 0.1295 -0.1859 0.6995 0.066 Uiso 1 1 calc R
C32 C 0.18914(16) -0.12115(11) 0.7716(3) 0.0509(8) Uani 1 1 d .
H32 H 0.1576 -0.0967 0.7193 0.061 Uiso 1 1 calc R
C33 C 0.25284(15) -0.10350(10) 0.8612(2) 0.0418(7) Uani 1 1 d .
C34 C 0.29800(17) -0.14258(11) 0.9337(3) 0.0558(9) Uani 1 1 d .
H34 H 0.3421 -0.1329 0.9938 0.067 Uiso 1 1 calc R
C35 C 0.27772(19) -0.19543(12) 0.9168(3) 0.0652(10) Uani 1 1 d .
H35 H 0.3085 -0.2210 0.9667 0.078 Uiso 1 1 calc R
O1A O 0.3831(3) -0.3881(2) 1.0773(4) 0.0804(16) Uani 0.50 1 d P
O2A O 0.3902(3) -0.2865(2) 1.0755(5) 0.0956(19) Uani 0.50 1 d P
C1A C 0.5000 -0.3897(3) 1.2500 0.0864(18) Uani 1 2 d S
H1A H 0.5000 -0.4271 1.2500 0.104 Uiso 1 2 calc SR
C2A C 0.4428(2) -0.36414(18) 1.1645(4) 0.0769(11) Uani 1 1 d .
C3A C 0.4435(2) -0.3103(2) 1.1633(4) 0.0790(12) Uani 1 1 d .
C4A C 0.5000 -0.2805(3) 1.2500 0.0904(19) Uani 1 2 d S
H4A H 0.5000 -0.2431 1.2500 0.109 Uiso 1 2 calc SR
O1B O 0.41927(15) -0.58470(11) 0.9954(2) 0.0816(8) Uani 1 1 d .
H1OB H 0.3758(17) -0.5696(12) 0.985(2) 0.050 Uiso 1 1 d .
C1B C 0.5126(2) -0.55142(16) 0.9828(3) 0.0688(10) Uani 1 1 d .
H1B H 0.5214 -0.5865 0.9711 0.083 Uiso 1 1 calc R
C2B C 0.45906(18) -0.54149(15) 0.9989(3) 0.0617(10) Uani 1 1 d .
C3B C 0.44600(19) -0.48997(16) 1.0165(3) 0.0664(10) Uani 1 1 d .
H3B H 0.4097 -0.4829 1.0279 0.080 Uiso 1 1 calc R
C1C C 0.4979(2) 0.1792(2) 0.3443(5) 0.113(2) Uani 1 1 d .
C2C C 0.49877(14) 0.22790(13) 0.2975(3) 0.0514(8) Uani 1 1 d .
C3C C 0.49777(19) 0.2771(2) 0.3437(4) 0.0905(15) Uani 1 1 d .
C4C C 0.4970(4) 0.2775(5) 0.4406(8) 0.195(6) Uani 1 1 d .
H4C H 0.4990 0.3087 0.4777 0.234 Uiso 1 1 calc R
C5C C 0.4934(6) 0.2303(8) 0.4713(10) 0.251(13) Uani 1 1 d .
H5C H 0.4891 0.2323 0.5317 0.301 Uiso 1 1 calc R
C6C C 0.4936(5) 0.1831(5) 0.4472(11) 0.228(10) Uani 1 1 d .
H6C H 0.4916 0.1539 0.4853 0.273 Uiso 1 1 calc R
C7C C 0.5003(3) 0.32501(18) 0.2928(4) 0.141(5) Uani 1 1 d .
H7C H 0.5025 0.3578 0.3254 0.169 Uiso 1 1 calc R
C8C C 0.5005(5) 0.1312(2) 0.2927(9) 0.244(12) Uani 1 1 d .
H8C H 0.5030 0.0984 0.3254 0.293 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 119.7(2) . .
C6 C1 C7 119.6(2) . .
C2 C1 C7 120.6(3) . .
C1 C2 C3 120.3(3) . .
C4 C3 C2 119.4(2) . .
C4 C3 C8 120.5(3) . .
C2 C3 C8 120.1(3) . .
C5 C4 C3 120.6(3) . .
C4 C5 C6 119.2(3) . .
C4 C5 C9 119.7(3) . .
C6 C5 C9 121.2(3) . .
C1 C6 C5 120.8(2) . .
O2 C7 O1 124.4(3) . .
O2 C7 C1 121.8(3) . .
O1 C7 C1 113.8(2) . .
O3 C8 O4 124.4(3) . .
O3 C8 C3 122.0(3) . .
O4 C8 C3 113.5(3) . .
O6 C9 O5 123.2(3) . .
O6 C9 C5 125.3(3) . .
O5 C9 C5 111.5(3) . .
O11 C11 C12 120.9(2) . .
O11 C11 C16 119.6(2) . .
C12 C11 C16 119.5(2) . .
C18 C12 C11 115.9(2) . .
C18 C12 C13 125.5(2) . .
C11 C12 C13 118.6(2) . .
C12 C13 C14 113.9(2) . .
C13 C14 C15 111.6(3) . .
C16 C15 C14 112.8(2) . .
C17 C16 C15 126.5(2) . .
C17 C16 C11 115.7(2) . .
C15 C16 C11 117.8(2) . .
C16 C17 C23 130.7(3) . .
C12 C18 C33 130.2(3) . .
C25 N21 C21 117.6(2) . .
N21 C21 C22 123.3(3) . .
C21 C22 C23 119.8(3) . .
C24 C23 C22 115.9(2) . .
C24 C23 C17 117.8(2) . .
C22 C23 C17 126.4(3) . .
C25 C24 C23 120.7(3) . .
N21 C25 C24 122.6(3) . .
C31 N31 C35 118.3(3) . .
N31 C31 C32 122.8(3) . .
C31 C32 C33 119.8(3) . .
C32 C33 C34 116.7(3) . .
C32 C33 C18 125.7(3) . .
C34 C33 C18 117.6(3) . .
C35 C34 C33 120.1(3) . .
N31 C35 C34 122.2(3) . .
C2A C1A C2A 124.5(6) 2_657 .
C3A C2A C1A 117.7(5) . .
C3A C2A O1A 115.6(4) . .
C1A C2A O1A 126.7(5) . .
O2A C3A C2A 116.7(5) . .
O2A C3A C4A 121.8(5) . .
C2A C3A C4A 121.5(5) . .
C3A C4A C3A 117.0(6) . 2_657
C2B C1B C3B 120.9(4) . 5_647
C1B C2B C3B 119.9(4) . .
C1B C2B O1B 117.6(4) . .
C3B C2B O1B 122.5(4) . .
C2B C3B C1B 119.3(4) . 5_647
C2C C1C C8C 117.2(6) . .
C2C C1C C6C 116.0(7) . .
C8C C1C C6C 126.8(7) . .
C1C C2C C3C 121.2(5) . .
C1C C2C C2C 119.6(4) . 2_655
C3C C2C C2C 119.1(3) . 2_655
C2C C3C C7C 118.1(5) . .
C2C C3C C4C 119.5(7) . .
C7C C3C C4C 122.4(7) . .
C5C C4C C3C 112.2(11) . .
C6C C5C C4C 140.5(15) . .
C5C C6C C1C 110.3(10) . .
C7C C7C C3C 122.7(3) 2_655 .
C8C C8C C1C 123.0(5) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.283(3) .
O2 C7 1.203(3) .
O3 C8 1.213(4) .
O4 C8 1.291(4) .
O5 C9 1.323(4) .
O6 C9 1.193(4) .
C1 C6 1.376(4) .
C1 C2 1.383(4) .
C1 C7 1.489(4) .
C2 C3 1.389(4) .
C3 C4 1.387(4) .
C3 C8 1.500(4) .
C4 C5 1.384(4) .
C5 C6 1.388(4) .
C5 C9 1.478(4) .
O11 C11 1.218(3) .
C11 C12 1.494(4) .
C11 C16 1.500(4) .
C12 C18 1.339(4) .
C12 C13 1.493(4) .
C13 C14 1.500(4) .
C14 C15 1.503(4) .
C15 C16 1.497(4) .
C16 C17 1.339(4) .
C17 C23 1.464(4) .
C18 C33 1.469(4) .
N21 C25 1.327(4) .
N21 C21 1.333(4) .
C21 C22 1.369(4) .
C22 C23 1.393(4) .
C23 C24 1.392(4) .
C24 C25 1.367(4) .
N31 C31 1.323(4) .
N31 C35 1.330(4) .
C31 C32 1.369(4) .
C32 C33 1.383(4) .
C33 C34 1.387(4) .
C34 C35 1.369(4) .
O1A C2A 1.383(6) .
O2A C3A 1.325(7) .
C1A C2A 1.367(5) 2_657
C1A C2A 1.367(5) .
C2A C3A 1.338(6) .
C3A C4A 1.419(5) .
C4A C3A 1.419(5) 2_657
O1B C2B 1.379(4) .
C1B C2B 1.364(5) .
C1B C3B 1.382(5) 5_647
C2B C3B 1.369(5) .
C3B C1B 1.382(5) 5_647
C1C C2C 1.392(5) .
C1C C8C 1.426(11) .
C1C C6C 1.547(16) .
C2C C3C 1.401(5) .
C2C C2C 1.405(7) 2_655
C3C C7C 1.418(8) .
C3C C4C 1.413(10) .
C4C C5C 1.274(18) .
C5C C6C 1.22(2) .
C7C C7C 1.233(15) 2_655
C8C C8C 1.23(3) 2_655
