#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/17/7101762.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_7101762
loop_
_publ_author_name
'Katz, Jeffrey L'
'Geller, Bram J'
'Foster, Peter D'
_publ_section_title
;
 Oxacalixarenes and oxacyclophanes containing 1,8-naphthyridines: a new
 class of molecular tweezers with concave-surface functionality.
;
_journal_issue                   10
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1026
_journal_page_last               1028
_journal_paper_doi               10.1039/b615336d
_journal_year                    2007
_chemical_formula_moiety         'C36.50 H20 Cl N4 O5'
_chemical_formula_sum            'C36.5 H20 Cl N4 O5'
_chemical_formula_weight         630.02
_chemical_melting_point_gt       533
_chemical_name_common            'compound 6'
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.3880(10)
_cell_angle_beta                 107.1250(10)
_cell_angle_gamma                111.1100(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6887(8)
_cell_length_b                   13.1957(10)
_cell_length_c                   13.4844(10)
_cell_measurement_reflns_used    5256
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.36
_cell_volume                     1455.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      180(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_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  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13087
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0802P)²+0.1740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                4971
_reflns_number_total             6628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b615336d.txt
_cod_data_source_block           624761
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>533K' was changed to
'533' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

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      P-1
_cod_original_formula_sum        'C36.50 H20 Cl N4 O5'
_cod_database_code               7101762
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 1.2753(2) 0.50790(15) 0.20934(14) 0.0357(4) Uani 1 1 d .
C2 C 1.3431(2) 0.51235(16) 0.12950(15) 0.0392(4) Uani 1 1 d .
H2 H 1.4554 0.5544 0.1496 0.047 Uiso 1 1 calc R
C3 C 1.2418(2) 0.45443(16) 0.02346(15) 0.0395(4) Uani 1 1 d .
H3 H 1.2828 0.4552 -0.0325 0.047 Uiso 1 1 calc R
C4 C 1.0747(2) 0.39265(14) -0.00426(14) 0.0337(4) Uani 1 1 d .
C5 C 0.9567(2) 0.33516(15) -0.11178(14) 0.0385(4) Uani 1 1 d .
H5 H 0.9874 0.3333 -0.1726 0.046 Uiso 1 1 calc R
C6 C 0.7987(2) 0.28227(15) -0.12845(14) 0.0372(4) Uani 1 1 d .
H6 H 0.7170 0.2431 -0.2002 0.045 Uiso 1 1 calc R
C7 C 0.7613(2) 0.28808(14) -0.03467(13) 0.0336(4) Uani 1 1 d .
C8 C 0.55707(19) 0.21637(15) 0.03211(13) 0.0340(4) Uani 1 1 d .
C9 C 0.4705(2) 0.26986(16) 0.06546(15) 0.0417(4) Uani 1 1 d .
H9 H 0.4480 0.3231 0.0327 0.050 Uiso 1 1 calc R
C10 C 0.4182(2) 0.24516(18) 0.14565(16) 0.0456(5) Uani 1 1 d .
H10 H 0.3592 0.2817 0.1685 0.055 Uiso 1 1 calc R
C11 C 0.4505(2) 0.16575(15) 0.19551(14) 0.0357(4) Uani 1 1 d .
C12 C 0.3988(2) 0.13727(18) 0.27894(16) 0.0461(5) Uani 1 1 d .
H12 H 0.3396 0.1725 0.3036 0.055 Uiso 1 1 calc R
C13 C 0.4320(2) 0.06059(17) 0.32432(15) 0.0428(4) Uani 1 1 d .
H13 H 0.3968 0.0425 0.3803 0.051 Uiso 1 1 calc R
C14 C 0.51873(19) 0.00841(14) 0.28789(13) 0.0325(4) Uani 1 1 d .
C15 C 0.67449(19) -0.04290(14) 0.42331(13) 0.0308(3) Uani 1 1 d .
C16 C 0.6948(2) -0.13372(14) 0.45787(14) 0.0342(4) Uani 1 1 d .
H16 H 0.6207 -0.2116 0.4180 0.041 Uiso 1 1 calc R
C17 C 0.8247(2) -0.10484(14) 0.55029(14) 0.0341(4) Uani 1 1 d .
H17 H 0.8435 -0.1630 0.5761 0.041 Uiso 1 1 calc R
C18 C 0.93185(19) 0.01182(14) 0.60795(13) 0.0314(3) Uani 1 1 d .
C19 C 1.0700(2) 0.05210(16) 0.70544(14) 0.0379(4) Uani 1 1 d .
H19 H 1.0937 -0.0008 0.7382 0.045 Uiso 1 1 calc R
C20 C 1.1685(2) 0.16578(16) 0.75214(14) 0.0381(4) Uani 1 1 d .
H20 H 1.2617 0.1944 0.8176 0.046 Uiso 1 1 calc R
C21 C 1.12685(19) 0.24041(14) 0.69945(13) 0.0317(4) Uani 1 1 d .
C22 C 1.21976(19) 0.42729(14) 0.68343(13) 0.0334(4) Uani 1 1 d .
C23 C 1.1704(2) 0.51034(16) 0.71550(15) 0.0403(4) Uani 1 1 d .
H23 H 1.1375 0.5137 0.7753 0.048 Uiso 1 1 calc R
C24 C 1.1703(2) 0.58686(16) 0.65935(16) 0.0440(4) Uani 1 1 d .
H24 H 1.1370 0.6437 0.6808 0.053 Uiso 1 1 calc R
C25 C 1.2185(2) 0.58337(14) 0.57025(14) 0.0358(4) Uani 1 1 d .
C26 C 1.2215(2) 0.66271(16) 0.51158(16) 0.0450(4) Uani 1 1 d .
H26 H 1.1888 0.7204 0.5318 0.054 Uiso 1 1 calc R
C27 C 1.2705(2) 0.65737(16) 0.42649(16) 0.0445(4) Uani 1 1 d .
H27 H 1.2723 0.7110 0.3878 0.053 Uiso 1 1 calc R
C28 C 1.31784(19) 0.57223(16) 0.39690(14) 0.0378(4) Uani 1 1 d .
C29 C 1.02188(19) 0.39210(14) 0.08288(13) 0.0317(4) Uani 1 1 d .
C30 C 0.59102(19) 0.13916(15) 0.07686(13) 0.0337(4) Uani 1 1 d .
H30 H 0.6497 0.1036 0.0520 0.040 Uiso 1 1 calc R
C31 C 0.53909(18) 0.11208(14) 0.15999(13) 0.0308(3) Uani 1 1 d .
C32 C 0.57104(19) 0.03218(14) 0.20821(13) 0.0334(4) Uani 1 1 d .
H32 H 0.6291 -0.0049 0.1848 0.040 Uiso 1 1 calc R
C33 C 0.90044(18) 0.09501(14) 0.56464(13) 0.0286(3) Uani 1 1 d .
C34 C 1.2674(2) 0.41997(14) 0.59824(13) 0.0343(4) Uani 1 1 d .
H34 H 1.3012 0.3627 0.5789 0.041 Uiso 1 1 calc R
C35 C 1.26681(18) 0.49722(14) 0.53847(13) 0.0316(4) Uani 1 1 d .
C36 C 1.3164(2) 0.49356(15) 0.44958(14) 0.0370(4) Uani 1 1 d .
H36 H 1.3485 0.4363 0.4269 0.044 Uiso 1 1 calc R
N1 N 1.12425(16) 0.44939(13) 0.18982(11) 0.0350(3) Uani 1 1 d .
N2 N 0.86425(16) 0.33784(12) 0.06626(11) 0.0335(3) Uani 1 1 d .
N3 N 0.76973(16) 0.06611(11) 0.47194(11) 0.0309(3) Uani 1 1 d .
N4 N 0.99945(15) 0.20916(12) 0.61148(11) 0.0308(3) Uani 1 1 d .
O1 O 1.37969(14) 0.57317(12) 0.31418(10) 0.0449(3) Uani 1 1 d .
O2 O 0.60026(14) 0.23883(11) -0.05499(9) 0.0398(3) Uani 1 1 d .
O3 O 0.54215(14) -0.07687(10) 0.32998(9) 0.0375(3) Uani 1 1 d .
O4 O 1.23074(14) 0.35425(10) 0.74746(9) 0.0384(3) Uani 1 1 d .
C37 C 0.0169(10) 1.0105(8) -0.0376(6) 0.115(3) Uani 0.50 1 d P
Cl1 Cl -0.0496(3) 1.08734(16) -0.0294(2) 0.1141(7) Uani 0.50 1 d P
Cl2 Cl -0.0424(4) 1.0900(3) 0.0593(3) 0.1496(10) Uani 0.50 1 d P
O5 O 0.0262(4) 0.2253(3) 0.2558(3) 0.1608(13) 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 O1 118.91(15) . .
N1 C1 C2 125.49(16) . .
O1 C1 C2 115.59(15) . .
C3 C2 C1 117.48(16) . .
C2 C3 C4 120.06(16) . .
C5 C4 C29 117.48(15) . .
C5 C4 C3 125.23(16) . .
C29 C4 C3 117.25(16) . .
C6 C5 C4 119.95(16) . .
C5 C6 C7 117.13(16) . .
N2 C7 O2 118.67(15) . .
N2 C7 C6 125.92(16) . .
O2 C7 C6 115.38(14) . .
C30 C8 C9 121.95(16) . .
C30 C8 O2 120.25(15) . .
C9 C8 O2 117.68(15) . .
C10 C9 C8 119.46(16) . .
C9 C10 C11 121.07(17) . .
C12 C11 C10 123.17(16) . .
C12 C11 C31 118.39(16) . .
C10 C11 C31 118.45(15) . .
C13 C12 C11 121.25(17) . .
C12 C13 C14 119.46(16) . .
C32 C14 C13 121.87(16) . .
C32 C14 O3 119.24(15) . .
C13 C14 O3 118.74(15) . .
N3 C15 O3 119.35(14) . .
N3 C15 C16 125.93(15) . .
O3 C15 C16 114.73(14) . .
C17 C16 C15 117.24(15) . .
C16 C17 C18 119.84(15) . .
C17 C18 C19 124.85(15) . .
C17 C18 C33 117.86(14) . .
C19 C18 C33 117.29(15) . .
C20 C19 C18 120.20(15) . .
C19 C20 C21 117.30(15) . .
N4 C21 O4 118.77(14) . .
N4 C21 C20 125.50(16) . .
O4 C21 C20 115.72(14) . .
C34 C22 C23 122.14(17) . .
C34 C22 O4 119.64(15) . .
C23 C22 O4 118.06(16) . .
C24 C23 C22 118.80(17) . .
C23 C24 C25 121.55(17) . .
C24 C25 C26 122.63(17) . .
C24 C25 C35 118.58(16) . .
C26 C25 C35 118.78(17) . .
C27 C26 C25 120.96(18) . .
C26 C27 C28 119.28(18) . .
C36 C28 C27 122.34(17) . .
C36 C28 O1 118.98(17) . .
C27 C28 O1 118.54(17) . .
N2 C29 N1 114.78(14) . .
N2 C29 C4 122.55(15) . .
N1 C29 C4 122.63(15) . .
C8 C30 C31 119.95(16) . .
C30 C31 C32 121.79(15) . .
C30 C31 C11 119.12(15) . .
C32 C31 C11 119.09(15) . .
C14 C32 C31 119.94(16) . .
N4 C33 N3 115.18(13) . .
N4 C33 C18 122.48(14) . .
N3 C33 C18 122.33(14) . .
C22 C34 C35 120.06(16) . .
C34 C35 C36 122.16(15) . .
C34 C35 C25 118.85(16) . .
C36 C35 C25 118.97(16) . .
C28 C36 C35 119.68(17) . .
C1 N1 C29 117.00(15) . .
C7 N2 C29 116.94(14) . .
C15 N3 C33 116.78(14) . .
C21 N4 C33 117.18(14) . .
C1 O1 C28 117.81(13) . .
C7 O2 C8 117.46(12) . .
C15 O3 C14 117.80(12) . .
C21 O4 C22 117.32(12) . .
Cl1 C37 Cl1 137.3(5) . 2_575
Cl2 C37 Cl2 140.2(5) 2_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.301(2) .
C1 O1 1.362(2) .
C1 C2 1.416(2) .
C2 C3 1.353(3) .
C3 C4 1.417(2) .
C4 C5 1.410(2) .
C4 C29 1.413(2) .
C5 C6 1.361(3) .
C6 C7 1.411(2) .
C7 N2 1.298(2) .
C7 O2 1.374(2) .
C8 C30 1.363(2) .
C8 C9 1.392(3) .
C8 O2 1.4029(19) .
C9 C10 1.365(3) .
C10 C11 1.419(2) .
C11 C12 1.417(2) .
C11 C31 1.423(2) .
C12 C13 1.358(3) .
C13 C14 1.400(3) .
C14 C32 1.355(2) .
C14 O3 1.4066(19) .
C15 N3 1.303(2) .
C15 O3 1.3641(19) .
C15 C16 1.418(2) .
C16 C17 1.357(2) .
C17 C18 1.412(2) .
C18 C19 1.415(2) .
C18 C33 1.416(2) .
C19 C20 1.353(3) .
C20 C21 1.416(2) .
C21 N4 1.302(2) .
C21 O4 1.366(2) .
C22 C34 1.359(2) .
C22 C23 1.395(3) .
C22 O4 1.416(2) .
C23 C24 1.367(3) .
C24 C25 1.411(3) .
C25 C26 1.419(2) .
C25 C35 1.421(2) .
C26 C27 1.365(3) .
C27 C28 1.396(3) .
C28 C36 1.358(2) .
C28 O1 1.413(2) .
C29 N2 1.359(2) .
C29 N1 1.363(2) .
C30 C31 1.409(2) .
C31 C32 1.412(2) .
C33 N4 1.359(2) .
C33 N3 1.3636(19) .
C34 C35 1.409(2) .
C35 C36 1.416(2) .
C37 Cl1 1.768(10) 2_575
C37 Cl2 1.877(10) .
Cl1 C37 1.768(10) 2_575
