#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/47/7204720.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_7204720
loop_
_publ_author_name
'Nakamura, A.'
'Sato, T.'
'Kuroda, R.'
_publ_section_title
;
 Novel layered structures of the crystals based on
 C-methylcalix[4]resorcinarene formed at high temperatureElectronic
 supplementary information (ESI) available: Structures of compounds 8,
 9, 10 and 12 (4 figures). See
 http://www.rsc.org/suppdata/ce/b3/b307471d/
;
_journal_issue                   56
_journal_name_full               CrystEngComm
_journal_page_first              318
_journal_paper_doi               10.1039/b307471d
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C33 H34 N2 O4.5'
_chemical_formula_weight         530.62
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            8
_cell_length_a                   15.9821(16)
_cell_length_b                   14.3963(15)
_cell_length_c                   23.765(2)
_cell_measurement_reflns_used    312866
_cell_measurement_temperature    116(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      1.90
_cell_volume                     5467.9(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      116(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω 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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32866
_diffrn_reflns_theta_full        27.91
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.252
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6439
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1048P)²+6.8270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2052
_reflns_number_gt                4594
_reflns_number_total             6439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b307471d.txt
_cod_data_source_block           nakamura9
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        5468.0(10)
_cod_original_sg_symbol_H-M      Pbcn
_cod_original_formula_sum        'C33 H34 N2 O4.50'
_cod_database_code               7204720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.83715(13) 0.14276(16) 0.26446(9) 0.0208(5) Uani 1 1 d . . .
H1 H 0.8730 0.1933 0.2610 0.025 Uiso 1 1 calc R . .
C3 C 0.77173(15) 0.02932(19) 0.32218(10) 0.0284(6) Uani 1 1 d . . .
C4 C 0.73425(18) -0.0076(2) 0.27442(12) 0.0389(7) Uani 1 1 d . . .
H4 H 0.6992 -0.0589 0.2778 0.047 Uiso 1 1 calc R . .
C5 C 0.74837(16) 0.0310(2) 0.22186(11) 0.0345(6) Uani 1 1 d . . .
C6 C 0.80059(14) 0.10770(18) 0.21555(10) 0.0245(5) Uani 1 1 d . . .
C7 C 0.81774(14) 0.15184(18) 0.15850(10) 0.0251(5) Uani 1 1 d . . .
H7 H 0.7711 0.1346 0.1339 0.030 Uiso 1 1 calc R . .
C8 C 0.81899(17) 0.25810(19) 0.16128(11) 0.0313(6) Uani 1 1 d . . .
H8A H 0.8301 0.2828 0.1245 0.047 Uiso 1 1 calc R . .
H8B H 0.8620 0.2779 0.1868 0.047 Uiso 1 1 calc R . .
H8C H 0.7657 0.2802 0.1742 0.047 Uiso 1 1 calc R . .
O9 O 0.75386(11) -0.01407(14) 0.37214(8) 0.0337(5) Uani 1 1 d . . .
H9 H 0.7912 -0.0033 0.3949 0.051 Uiso 1 1 calc R . .
O10 O 0.70709(14) -0.00897(18) 0.17721(8) 0.0501(6) Uani 1 1 d . . .
H10 H 0.7362 -0.0052 0.1489 0.075 Uiso 1 1 calc R . .
C11 C 0.97620(14) 0.14855(16) 0.14120(9) 0.0205(5) Uani 1 1 d . . .
H11 H 0.9805 0.2016 0.1634 0.025 Uiso 1 1 calc R . .
C12 C 0.89684(14) 0.11104(17) 0.13226(9) 0.0219(5) Uani 1 1 d . . .
C13 C 0.89175(14) 0.03170(17) 0.09859(10) 0.0229(5) Uani 1 1 d . . .
C14 C 0.96294(15) -0.00603(17) 0.07429(10) 0.0243(5) Uani 1 1 d . . .
H14 H 0.9583 -0.0573 0.0507 0.029 Uiso 1 1 calc R . .
C15 C 1.04101(14) 0.03214(17) 0.08497(10) 0.0229(5) Uani 1 1 d . . .
C16 C 1.04943(14) 0.11111(16) 0.11880(9) 0.0204(5) Uani 1 1 d . . .
C17 C 1.13564(14) 0.15156(16) 0.13025(9) 0.0213(5) Uani 1 1 d . . .
H17 H 1.1707 0.1353 0.0979 0.026 Uiso 1 1 calc R . .
C18 C 1.13454(16) 0.25805(17) 0.13352(11) 0.0273(5) Uani 1 1 d . . .
H18A H 1.1902 0.2804 0.1405 0.041 Uiso 1 1 calc R . .
H18B H 1.0983 0.2773 0.1636 0.041 Uiso 1 1 calc R . .
H18C H 1.1144 0.2830 0.0986 0.041 Uiso 1 1 calc R . .
O19 O 0.81478(10) -0.00815(13) 0.08954(8) 0.0294(4) Uani 1 1 d . . .
H19 H 0.8210 -0.0622 0.0796 0.044 Uiso 1 1 calc R . .
O20 O 1.11136(10) -0.00649(12) 0.06151(8) 0.0281(4) Uani 1 1 d . . .
H20 H 1.1029 -0.0617 0.0551 0.042 Uiso 1 1 calc R . .
C2 C 0.82352(14) 0.10705(17) 0.31813(10) 0.0217(5) Uani 1 1 d . . .
C31 C 1.13157(14) -0.62099(18) -0.04486(10) 0.0254(5) Uani 1 1 d . . .
C32 C 1.09753(16) -0.66669(19) -0.09102(11) 0.0291(6) Uani 1 1 d . . .
H32 H 1.0642 -0.6344 -0.1164 0.035 Uiso 1 1 calc R . .
C33 C 1.11328(16) -0.7602(2) -0.09916(11) 0.0318(6) Uani 1 1 d . . .
H33 H 1.0894 -0.7893 -0.1302 0.038 Uiso 1 1 calc R . .
C35 C 1.19582(16) -0.76621(18) -0.02117(11) 0.0293(6) Uani 1 1 d . . .
H35 H 1.2302 -0.7999 0.0029 0.035 Uiso 1 1 calc R . .
N34 N 1.16102(13) -0.81078(15) -0.06474(9) 0.0291(5) Uani 1 1 d . . .
C36 C 1.18359(15) -0.67319(18) -0.00996(11) 0.0270(5) Uani 1 1 d . . .
H36 H 1.2099 -0.6455 0.0207 0.032 Uiso 1 1 calc R . .
C37 C 1.11292(15) -0.52295(18) -0.03444(11) 0.0277(5) Uani 1 1 d . . .
H37 H 1.0922 -0.4884 -0.0644 0.033 Uiso 1 1 calc R . .
C38 C 1.12314(15) -0.47909(18) 0.01430(11) 0.0270(5) Uani 1 1 d . . .
H38 H 1.1422 -0.5141 0.0446 0.032 Uiso 1 1 calc R . .
C39 C 1.10692(14) -0.38020(18) 0.02446(10) 0.0250(5) Uani 1 1 d . . .
C40 C 1.13096(16) -0.34025(19) 0.07557(10) 0.0287(5) Uani 1 1 d . . .
H40 H 1.1526 -0.3772 0.1041 0.034 Uiso 1 1 calc R . .
C41 C 1.12242(16) -0.24600(19) 0.08350(11) 0.0302(6) Uani 1 1 d . . .
H41 H 1.1392 -0.2209 0.1177 0.036 Uiso 1 1 calc R . .
N42 N 1.09126(13) -0.18863(15) 0.04456(9) 0.0293(5) Uani 1 1 d . . .
C43 C 1.06528(17) -0.22721(19) -0.00372(10) 0.0300(6) Uani 1 1 d . . .
H43 H 1.0418 -0.1887 -0.0309 0.036 Uiso 1 1 calc R . .
C44 C 1.07148(16) -0.32044(18) -0.01528(10) 0.0278(5) Uani 1 1 d . . .
H44 H 1.0522 -0.3437 -0.0494 0.033 Uiso 1 1 calc R . .
O61 O 0.0481(3) 0.4223(4) 0.3508(2) 0.0589(13) Uani 0.50 1 d P . .
H61 H 0.0942 0.4431 0.3424 0.088 Uiso 0.50 1 calc PR . .
C62 C -0.0130(4) 0.4580(5) 0.3132(3) 0.0500(16) Uani 0.50 1 d P . .
H62A H -0.0077 0.5250 0.3107 0.060 Uiso 0.50 1 calc PR . .
H62B H -0.0685 0.4436 0.3271 0.060 Uiso 0.50 1 calc PR . .
C63 C 0.0000 0.4112(4) 0.2500 0.0718(17) Uani 1 2 d S . .
H63A H -0.0406 0.4366 0.2245 0.108 Uiso 0.50 1 calc PR . .
H63B H -0.0072 0.3452 0.2524 0.108 Uiso 0.50 1 calc PR . .
H63C H 0.0553 0.4249 0.2365 0.108 Uiso 0.50 1 calc PR . .
C71 C 0.0174(5) 0.8672(4) 0.2496(7) 0.057(3) Uani 0.50 1 d PD . .
C72 C -0.0428(4) 0.8044(4) 0.2605(3) 0.0420(14) Uani 0.50 1 d PD . .
H72 H -0.0974 0.8246 0.2664 0.050 Uiso 0.50 1 calc PR . .
C73 C -0.0252(3) 0.7103(5) 0.2631(3) 0.0478(18) Uani 0.50 1 d PD . .
C74 C 0.0574(4) 0.6830(5) 0.2557(3) 0.0539(18) Uani 0.50 1 d PD . .
H74 H 0.0717 0.6207 0.2596 0.065 Uiso 0.50 1 calc PR . .
C75 C 0.1193(4) 0.7477(5) 0.2425(3) 0.059(2) Uani 0.50 1 d PD . .
H75 H 0.1737 0.7282 0.2350 0.071 Uiso 0.50 1 calc PR . .
C76 C 0.0992(4) 0.8411(5) 0.2407(3) 0.0531(19) Uani 0.50 1 d PD . .
H76 H 0.1402 0.8854 0.2337 0.064 Uiso 0.50 1 calc PR . .
C77 C 0.0000 0.9707(3) 0.2500 0.0699(16) Uani 1 2 d SD . .
H77A H -0.0593 0.9811 0.2479 0.105 Uiso 0.50 1 calc PR . .
H77B H 0.0268 0.9993 0.2182 0.105 Uiso 0.50 1 calc PR . .
H77C H 0.0215 0.9974 0.2841 0.105 Uiso 0.50 1 calc PR . .
C78 C -0.0928(5) 0.6407(7) 0.2758(4) 0.082(3) Uani 0.50 1 d PD . .
H78A H -0.1056 0.6061 0.2424 0.122 Uiso 0.50 1 calc PR . .
H78B H -0.1421 0.6727 0.2884 0.122 Uiso 0.50 1 calc PR . .
H78C H -0.0740 0.5991 0.3047 0.122 Uiso 0.50 1 calc PR . .
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
_geom_angle_publ_flag
C2 C1 C6 124.3(2) . . ?
O9 C3 C4 116.3(2) . . ?
O9 C3 C2 123.3(2) . . ?
C4 C3 C2 120.4(2) . . ?
C5 C4 C3 120.8(3) . . ?
O10 C5 C4 116.7(2) . . ?
O10 C5 C6 122.4(2) . . ?
C4 C5 C6 120.9(2) . . ?
C5 C6 C1 116.6(2) . . ?
C5 C6 C7 122.3(2) . . ?
C1 C6 C7 121.0(2) . . ?
C6 C7 C12 110.62(19) . . ?
C6 C7 C8 112.4(2) . . ?
C12 C7 C8 113.0(2) . . ?
C16 C11 C12 123.7(2) . . ?
C11 C12 C13 117.2(2) . . ?
C11 C12 C7 122.8(2) . . ?
C13 C12 C7 120.0(2) . . ?
O19 C13 C14 120.4(2) . . ?
O19 C13 C12 118.9(2) . . ?
C14 C13 C12 120.7(2) . . ?
C13 C14 C15 120.4(2) . . ?
O20 C15 C14 120.1(2) . . ?
O20 C15 C16 118.9(2) . . ?
C14 C15 C16 120.9(2) . . ?
C11 C16 C15 116.9(2) . . ?
C11 C16 C17 123.0(2) . . ?
C15 C16 C17 120.1(2) . . ?
C16 C17 C2 111.69(18) . 3_755 ?
C16 C17 C18 112.4(2) . . ?
C2 C17 C18 112.48(19) 3_755 . ?
C1 C2 C3 116.9(2) . . ?
C1 C2 C17 120.9(2) . 3_755 ?
C3 C2 C17 122.2(2) . 3_755 ?
C32 C31 C36 116.6(2) . . ?
C32 C31 C37 120.7(2) . . ?
C36 C31 C37 122.7(2) . . ?
C33 C32 C31 120.0(2) . . ?
N34 C33 C32 123.3(2) . . ?
N34 C35 C36 123.8(2) . . ?
C33 N34 C35 116.7(2) . . ?
C35 C36 C31 119.5(2) . . ?
C38 C37 C31 125.5(2) . . ?
C37 C38 C39 125.6(2) . . ?
C44 C39 C40 116.4(2) . . ?
C44 C39 C38 123.9(2) . . ?
C40 C39 C38 119.6(2) . . ?
C41 C40 C39 119.8(2) . . ?
N42 C41 C40 123.5(2) . . ?
C41 N42 C43 116.9(2) . . ?
N42 C43 C44 123.6(2) . . ?
C43 C44 C39 119.7(2) . . ?
O61 C62 C63 109.7(5) . . ?
C72 C71 C76 121.7(6) . . ?
C72 C71 C77 121.9(6) . . ?
C76 C71 C77 116.4(6) . . ?
C71 C72 C73 121.4(6) . . ?
C72 C73 C74 117.7(5) . . ?
C72 C73 C78 120.9(6) . . ?
C74 C73 C78 121.4(7) . . ?
C73 C74 C75 120.9(6) . . ?
C76 C75 C74 119.4(6) . . ?
C71 C76 C75 118.8(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.392(3) . ?
C1 C6 1.395(3) . ?
C3 O9 1.372(3) . ?
C3 C4 1.389(4) . ?
C3 C2 1.395(3) . ?
C4 C5 1.386(4) . ?
C5 O10 1.376(3) . ?
C5 C6 1.392(4) . ?
C6 C7 1.522(3) . ?
C7 C12 1.527(3) . ?
C7 C8 1.531(4) . ?
C11 C16 1.394(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.397(3) . ?
C13 O19 1.374(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.387(3) . ?
C15 O20 1.373(3) . ?
C15 C16 1.399(3) . ?
C16 C17 1.520(3) . ?
C17 C2 1.530(3) 3_755 ?
C17 C18 1.535(3) . ?
C2 C17 1.530(3) 3_755 ?
C31 C32 1.390(4) . ?
C31 C36 1.394(3) . ?
C31 C37 1.464(4) . ?
C32 C33 1.383(4) . ?
C33 N34 1.335(4) . ?
C35 N34 1.339(3) . ?
C35 C36 1.379(4) . ?
C37 C38 1.329(4) . ?
C38 C39 1.467(4) . ?
C39 C44 1.397(3) . ?
C39 C40 1.398(4) . ?
C40 C41 1.377(4) . ?
C41 N42 1.337(3) . ?
N42 C43 1.341(3) . ?
C43 C44 1.374(4) . ?
O61 C62 1.420(8) . ?
C62 C63 1.659(7) . ?
C71 C72 1.345(7) . ?
C71 C76 1.377(8) . ?
C71 C77 1.516(7) . ?
C72 C73 1.386(7) . ?
C73 C74 1.389(7) . ?
C73 C78 1.504(7) . ?
C74 C75 1.395(7) . ?
C75 C76 1.383(7) . ?
