#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:44:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178404 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/25/4022563.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_4022563
loop_
_publ_author_name
'Bao-Qing Ma'
'Yuegang Zhang'
'Philip Coppens'
_publ_section_title
;
 Multiple Conformations of Benzil in Resorcinarene-Based
 Supramolecular Host Matrixes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9467
_journal_page_last               9472
_journal_paper_doi               10.1021/jo035169k
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C76 H75 N8 O11'
_chemical_formula_weight         1276.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 103.368(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1489(13)
_cell_length_b                   22.831(3)
_cell_length_c                   13.3360(13)
_cell_measurement_temperature    90(1)
_cell_volume                     3302.6(6)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(1)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'SMART CCD 1000'
_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  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            74442
_diffrn_reflns_theta_full        31.25
_diffrn_reflns_theta_max         31.25
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.087
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1350
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         10230
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0633
_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)+(0.0837P)²+2.7620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                7756
_reflns_number_total             10230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo035169ksi20030821_121329.cif
_cod_data_source_block           p21m
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4022563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.23280(11) 0.64701(6) 0.51534(9) 0.0209(2) Uani 1 1 d .
O2 O 0.42479(10) 0.58163(5) 0.48345(9) 0.0193(2) Uani 1 1 d .
O3 O 0.78161(10) 0.57494(5) 0.34130(9) 0.0189(2) Uani 1 1 d .
O4 O 0.93025(11) 0.64711(6) 0.26610(10) 0.0222(3) Uani 1 1 d .
O5 O 0.2682(2) 0.7500 0.02685(15) 0.0320(4) Uani 1 2 d S
O6 O 0.2160(3) 0.65269(12) -0.1479(3) 0.0384(7) Uani 0.50 1 d P
O7 O 0.5830(4) 0.7500 0.5136(3) 0.1013(15) Uani 1 2 d SD
H7 H 0.5091 0.7500 0.4864 0.152 Uiso 1 2 calc SRD
N1 N 0.89960(12) 0.54915(6) 0.53008(10) 0.0188(3) Uani 1 1 d .
N2 N 1.40883(13) 0.43267(7) 1.33584(10) 0.0199(3) Uani 1 1 d .
N3 N 1.10138(13) 0.50173(6) 0.89129(10) 0.0198(3) Uani 1 1 d .
N4 N 1.18289(13) 0.49504(6) 0.98709(10) 0.0200(3) Uani 1 1 d .
C1 C 0.2299(2) 0.7500 0.50938(17) 0.0184(4) Uani 1 2 d S
C2 C 0.24381(13) 0.69729(7) 0.46160(12) 0.0164(3) Uani 1 1 d .
C3 C 0.26875(13) 0.69618(7) 0.36324(11) 0.0137(3) Uani 1 1 d .
C4 C 0.28198(18) 0.7500 0.31738(16) 0.0136(4) Uani 1 2 d S
H4A H 0.304(3) 0.7500 0.248(2) 0.015(7) Uiso 1 2 d S
C5 C 0.28041(13) 0.63864(6) 0.30827(11) 0.0132(3) Uani 1 1 d .
H5A H 0.2430(18) 0.6082(9) 0.3423(15) 0.015(5) Uiso 1 1 d .
C6 C 0.20446(14) 0.63879(7) 0.19655(12) 0.0163(3) Uani 1 1 d .
H6A H 0.2331(18) 0.6691(9) 0.1545(15) 0.016(5) Uiso 1 1 d .
C7 C 0.41485(13) 0.62271(6) 0.31705(11) 0.0129(3) Uani 1 1 d .
C8 C 0.48252(13) 0.59502(7) 0.40558(11) 0.0148(3) Uani 1 1 d .
C9 C 0.60460(14) 0.57888(7) 0.41399(11) 0.0160(3) Uani 1 1 d .
H9A H 0.645(2) 0.5583(10) 0.4721(17) 0.023(5) Uiso 1 1 d .
C10 C 0.66242(13) 0.59194(7) 0.33471(11) 0.0146(3) Uani 1 1 d .
C11 C 0.59935(13) 0.62097(6) 0.24562(11) 0.0135(3) Uani 1 1 d .
C12 C 0.47608(13) 0.63511(6) 0.23939(11) 0.0134(3) Uani 1 1 d .
H12A H 0.4310(19) 0.6556(9) 0.1777(16) 0.019(5) Uiso 1 1 d .
C13 C 0.66744(13) 0.63848(7) 0.16326(11) 0.0144(3) Uani 1 1 d .
H13A H 0.7285(18) 0.6063(9) 0.1627(15) 0.014(5) Uiso 1 1 d .
C14 C 0.58412(15) 0.63985(7) 0.05421(12) 0.0181(3) Uani 1 1 d .
H14B H 0.5199(19) 0.6686(9) 0.0441(16) 0.018(5) Uiso 1 1 d .
H14A H 0.632(2) 0.6484(10) 0.0032(17) 0.024(5) Uiso 1 1 d .
C15 C 0.73636(13) 0.69620(7) 0.19146(11) 0.0142(3) Uani 1 1 d .
C16 C 0.67684(19) 0.7500 0.17037(16) 0.0142(4) Uani 1 2 d S
H16A H 0.592(3) 0.7500 0.137(2) 0.019(7) Uiso 1 2 d S
C17 C 0.86226(14) 0.69727(7) 0.23996(12) 0.0167(3) Uani 1 1 d .
C18 C 0.9244(2) 0.7500 0.26274(17) 0.0182(4) Uani 1 2 d S
H18A H 1.011(3) 0.7500 0.295(2) 0.017(7) Uiso 1 2 d S
C19 C 0.88059(15) 0.50685(7) 0.59445(12) 0.0190(3) Uani 1 1 d .
C20 C 0.95969(14) 0.49648(7) 0.68893(12) 0.0175(3) Uani 1 1 d .
H20A H 0.942(2) 0.4661(11) 0.7338(18) 0.030(6) Uiso 1 1 d .
C21 C 1.06504(14) 0.53100(7) 0.71927(11) 0.0167(3) Uani 1 1 d .
C22 C 1.08547(15) 0.57467(8) 0.65228(12) 0.0197(3) Uani 1 1 d .
C23 C 1.00045(15) 0.58240(8) 0.55942(13) 0.0203(3) Uani 1 1 d .
H23A H 1.012(2) 0.6114(10) 0.5136(17) 0.025(5) Uiso 1 1 d .
C24 C 1.15162(14) 0.52083(7) 0.82044(12) 0.0179(3) Uani 1 1 d .
C25 C 1.28712(16) 0.53138(10) 0.83351(15) 0.0279(4) Uani 1 1 d .
C26 C 1.16199(14) 0.45007(7) 1.03822(11) 0.0161(3) Uani 1 1 d .
C27 C 1.06509(17) 0.40522(8) 0.99942(14) 0.0242(3) Uani 1 1 d .
C28 C 1.24640(14) 0.44364(7) 1.14182(11) 0.0156(3) Uani 1 1 d .
C29 C 1.22510(16) 0.40320(8) 1.21380(12) 0.0209(3) Uani 1 1 d .
H29A H 1.153(2) 0.3767(11) 1.2005(19) 0.035(6) Uiso 1 1 d .
C30 C 1.30786(16) 0.39941(8) 1.30905(13) 0.0238(3) Uani 1 1 d .
C31 C 1.42902(15) 0.47166(7) 1.26645(12) 0.0192(3) Uani 1 1 d .
C32 C 1.35145(15) 0.47850(7) 1.17005(12) 0.0186(3) Uani 1 1 d .
C33 C 0.0616(3) 0.7500 -0.0746(2) 0.0325(6) Uani 1 2 d S
C34 C 0.0043(3) 0.7500 0.00729(19) 0.0241(5) Uani 1 2 d S
C35 C -0.1228(3) 0.7500 -0.0125(2) 0.0321(6) Uani 1 2 d S
C36 C -0.1933(3) 0.7500 -0.1129(2) 0.0319(6) Uani 1 2 d S
C37 C -0.1365(3) 0.7500 -0.1948(2) 0.0334(6) Uani 1 2 d S
C38 C -0.0100(3) 0.7500 -0.1757(2) 0.0484(9) Uani 1 2 d S
C39 C 0.1973(3) 0.7500 -0.0530(3) 0.0705(16) Uani 1 2 d S
C40 C 0.2513(4) 0.70318(15) -0.1323(3) 0.0253(7) Uani 0.50 1 d P
C41 C 0.3530(3) 0.72010(16) -0.17601(18) 0.0625(9) Uani 1 1 d .
C42 C 0.4198(4) 0.69074(15) -0.2341(2) 0.0708(11) Uani 1 1 d .
C43 C 0.4886(2) 0.72003(10) -0.29146(17) 0.0367(5) Uani 1 1 d .
C44 C 0.6499(5) 0.7500 0.4381(3) 0.0580(11) Uani 1 2 d SD
C45 C 0.7824(6) 0.7500 0.4914(4) 0.0881(19) Uani 1 2 d S
H1A H 0.216(3) 0.7500 0.579(2) 0.022(7) Uiso 1 2 d S
H1 H 0.285(2) 0.6210(12) 0.5003(19) 0.035(6) Uiso 1 1 d .
H6C H 0.117(2) 0.6457(10) 0.1980(18) 0.027(6) Uiso 1 1 d .
H19A H 0.804(2) 0.4840(11) 0.5683(18) 0.034(6) Uiso 1 1 d .
H43A H 0.532(3) 0.7012(13) -0.339(2) 0.050(8) Uiso 1 1 d .
H31A H 1.504(2) 0.4958(10) 1.2889(16) 0.022(5) Uiso 1 1 d .
H32A H 1.373(2) 0.5084(10) 1.1223(17) 0.027(6) Uiso 1 1 d .
H14C H 0.542(2) 0.6011(10) 0.0381(17) 0.025(5) Uiso 1 1 d .
H6B H 0.213(2) 0.5995(11) 0.1626(18) 0.032(6) Uiso 1 1 d .
H34A H 0.058(4) 0.7500 0.079(3) 0.044(10) Uiso 1 2 d S
H30A H 1.292(2) 0.3726(12) 1.361(2) 0.038(7) Uiso 1 1 d .
H22A H 1.152(2) 0.6016(11) 0.6704(18) 0.030(6) Uiso 1 1 d .
H3 H 0.815(3) 0.5634(14) 0.406(2) 0.055(9) Uiso 1 1 d .
H36A H -0.284(4) 0.7500 -0.128(3) 0.039(10) Uiso 1 2 d S
H25C H 1.308(3) 0.5530(14) 0.780(2) 0.058(9) Uiso 1 1 d .
H4 H 0.884(2) 0.6217(12) 0.2849(19) 0.036(7) Uiso 1 1 d .
H35A H -0.164(4) 0.7500 0.045(4) 0.064(13) Uiso 1 2 d S
H27C H 0.995(3) 0.4220(14) 0.948(2) 0.058(9) Uiso 1 1 d .
H25B H 1.316(3) 0.5539(14) 0.895(2) 0.055(8) Uiso 1 1 d .
H37A H -0.181(4) 0.7500 -0.266(3) 0.054(12) Uiso 1 2 d S
H2 H 0.482(3) 0.5758(13) 0.544(2) 0.053(8) Uiso 1 1 d .
H27B H 1.028(3) 0.3904(15) 1.050(2) 0.060(9) Uiso 1 1 d .
H25A H 1.334(3) 0.4914(16) 0.841(3) 0.069(10) Uiso 1 1 d .
H27A H 1.099(3) 0.3729(18) 0.971(3) 0.081(11) Uiso 1 1 d .
H38A H 0.040(6) 0.7500 -0.226(5) 0.11(2) Uiso 1 2 d S
H42A H 0.427(4) 0.653(2) -0.236(4) 0.113(17) Uiso 1 1 d .
H45B H 0.866(2) 0.7201(11) 0.5331(18) 0.028(6) Uiso 1 1 d D
H44A H 0.633(4) 0.7136(19) 0.387(3) 0.102(14) Uiso 1 1 d .
H45A H 0.854(11) 0.7500 0.457(3) 0.21(4) Uiso 1 2 d SD
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
C23 N1 C19 117.90(13) . .
C30 N2 C31 117.29(14) . .
C24 N3 N4 114.18(13) . .
C26 N4 N3 114.48(13) . .
C2 C1 C2 120.4(2) 4_575 .
O1 C2 C1 116.90(14) . .
O1 C2 C3 122.26(14) . .
C1 C2 C3 120.84(15) . .
C4 C3 C2 117.25(15) . .
C4 C3 C5 121.24(13) . .
C2 C3 C5 121.51(13) . .
C3 C4 C3 123.42(19) 4_575 .
C7 C5 C3 111.18(12) . .
C7 C5 C6 112.85(12) . .
C3 C5 C6 112.08(12) . .
C12 C7 C8 117.26(13) . .
C12 C7 C5 122.50(12) . .
C8 C7 C5 120.24(13) . .
O2 C8 C9 120.02(13) . .
O2 C8 C7 118.87(13) . .
C9 C8 C7 121.06(13) . .
C8 C9 C10 119.92(13) . .
O3 C10 C9 120.28(13) . .
O3 C10 C11 118.61(13) . .
C9 C10 C11 121.09(13) . .
C12 C11 C10 117.04(13) . .
C12 C11 C13 122.94(13) . .
C10 C11 C13 119.95(13) . .
C7 C12 C11 123.59(13) . .
C11 C13 C15 110.75(12) . .
C11 C13 C14 113.24(12) . .
C15 C13 C14 112.06(12) . .
C16 C15 C17 117.17(15) . .
C16 C15 C13 121.44(13) . .
C17 C15 C13 121.39(13) . .
C15 C16 C15 123.64(19) 4_575 .
O4 C17 C18 116.73(14) . .
O4 C17 C15 122.49(14) . .
C18 C17 C15 120.78(15) . .
C17 C18 C17 120.4(2) 4_575 .
N1 C19 C20 123.04(15) . .
C19 C20 C21 119.02(14) . .
C22 C21 C20 118.06(14) . .
C22 C21 C24 121.78(14) . .
C20 C21 C24 120.16(14) . .
C23 C22 C21 119.01(15) . .
N1 C23 C22 122.95(15) . .
N3 C24 C21 114.85(14) . .
N3 C24 C25 124.71(14) . .
C21 C24 C25 120.42(14) . .
N4 C26 C28 114.75(14) . .
N4 C26 C27 124.81(14) . .
C28 C26 C27 120.41(14) . .
C29 C28 C32 117.34(14) . .
C29 C28 C26 122.27(14) . .
C32 C28 C26 120.39(14) . .
C30 C29 C28 119.27(15) . .
N2 C30 C29 123.33(16) . .
N2 C31 C32 123.26(15) . .
C31 C32 C28 119.51(15) . .
C34 C33 C38 119.7(3) . .
C34 C33 C39 119.0(3) . .
C38 C33 C39 121.4(3) . .
C35 C34 C33 119.3(3) . .
C34 C35 C36 120.8(3) . .
C37 C36 C35 120.1(3) . .
C38 C37 C36 119.5(3) . .
C37 C38 C33 120.7(3) . .
O5 C39 C33 128.7(3) . .
O5 C39 C40 107.6(3) . 4_575
C33 C39 C40 111.8(2) . 4_575
O5 C39 C40 107.6(3) . .
C33 C39 C40 111.8(2) . .
C40 C39 C40 77.5(3) 4_575 .
O6 C40 C41 115.9(3) . .
O6 C40 C39 123.4(3) . .
C41 C40 C39 120.3(3) . .
C41 C41 C42 119.34(19) 4_575 .
C41 C41 C40 105.5(2) 4_575 .
C42 C41 C40 132.8(3) . .
C41 C42 C43 121.6(3) . .
C43 C43 C42 119.09(18) 4_575 .
O7 C44 C45 107.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3736(19) .
O2 C8 1.3767(18) .
O3 C10 1.3676(18) .
O4 C17 1.3731(19) .
O5 C39 1.170(4) .
O6 C40 1.220(4) .
O7 C44 1.385(5) .
N1 C23 1.338(2) .
N1 C19 1.341(2) .
N2 C30 1.336(2) .
N2 C31 1.340(2) .
N3 C24 1.281(2) .
N3 N4 1.3945(18) .
N4 C26 1.283(2) .
C1 C2 1.3872(19) 4_575
C1 C2 1.3872(19) .
C2 C3 1.403(2) .
C3 C4 1.3956(18) .
C3 C5 1.524(2) .
C4 C3 1.3955(18) 4_575
C5 C7 1.520(2) .
C5 C6 1.534(2) .
C7 C12 1.395(2) .
C7 C8 1.397(2) .
C8 C9 1.389(2) .
C9 C10 1.392(2) .
C10 C11 1.400(2) .
C11 C12 1.395(2) .
C11 C13 1.526(2) .
C13 C15 1.528(2) .
C13 C14 1.534(2) .
C15 C16 1.3936(18) .
C15 C17 1.403(2) .
C16 C15 1.3936(18) 4_575
C17 C18 1.3873(19) .
C18 C17 1.3873(19) 4_575
C19 C20 1.381(2) .
C20 C21 1.394(2) .
C21 C22 1.392(2) .
C21 C24 1.485(2) .
C22 C23 1.386(2) .
C24 C25 1.500(2) .
C26 C28 1.488(2) .
C26 C27 1.492(2) .
C28 C29 1.391(2) .
C28 C32 1.394(2) .
C29 C30 1.389(2) .
C31 C32 1.382(2) .
C33 C34 1.387(4) .
C33 C38 1.399(4) .
C33 C39 1.473(5) .
C34 C35 1.381(4) .
C35 C36 1.387(4) .
C36 C37 1.383(4) .
C37 C38 1.374(5) .
C39 C40 1.709(4) 4_575
C39 C40 1.709(4) .
C40 C41 1.442(4) .
C41 C41 1.366(7) 4_575
C41 C42 1.368(4) .
C42 C43 1.375(3) .
C43 C43 1.369(5) 4_575
C44 C45 1.484(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.89(3) 1.85(3) 2.7225(18) 165(2) .
O2 H2 N2 0.91(3) 1.79(3) 2.6997(17) 177(3) 3_767
O3 H3 N1 0.89(3) 1.74(3) 2.6238(17) 170(3) .
O4 H4 O3 0.85(3) 1.85(3) 2.6898(18) 171(3) .
