#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/07/1100724.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_1100724
loop_
_publ_author_name
'Tara J. Burchell'
'Richard J. Puddephatt'
_publ_section_title
;

Self-Assembly of Chiral Coordination Polymers and Macrocycles: A Metal

Template Effect on the Polymer-Macrocycle Equilibrium

;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3718
_journal_page_last               3730
_journal_paper_doi               10.1021/ic050097w
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C36 H30 N4 O3'
_chemical_formula_weight         566.64
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.54(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5809(19)
_cell_length_b                   18.196(4)
_cell_length_c                   17.263(4)
_cell_measurement_temperature    150(2)
_cell_volume                     2899.5(12)
_computing_cell_refinement       'Nonius DENZO'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phiω 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  0.044
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28792
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9592
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6657
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0863P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1667
_reflns_number_gt                4039
_reflns_number_total             6657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050097wsi20050217_082525_01.cif
_cod_data_source_block           rac-1
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2899.3(10)
_cod_database_code               1100724
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C5 C 0.8327(2) -0.18279(11) 0.41685(12) 0.0394(5) Uani 1 1 d . . .
H5A H 0.8556 -0.2129 0.4635 0.047 Uiso 1 1 calc R . .
C1 C 0.8832(2) -0.11163(11) 0.42426(12) 0.0360(5) Uani 1 1 d . . .
H1B H 0.9418 -0.0940 0.4742 0.043 Uiso 1 1 calc R . .
C2 C 0.84682(19) -0.06616(10) 0.35748(11) 0.0295(4) Uani 1 1 d . . .
C3 C 0.7652(2) -0.09529(11) 0.28598(12) 0.0366(5) Uani 1 1 d . . .
H3A H 0.7377 -0.0657 0.2390 0.044 Uiso 1 1 calc R . .
C4 C 0.7238(2) -0.16849(11) 0.28382(13) 0.0404(5) Uani 1 1 d . . .
H4A H 0.6713 -0.1885 0.2336 0.048 Uiso 1 1 calc R . .
N1 N 0.75316(18) -0.21223(9) 0.34770(10) 0.0374(4) Uani 1 1 d . . .
C6 C 0.8996(2) 0.01161(10) 0.36525(12) 0.0307(4) Uani 1 1 d . . .
O1 O 1.02112(14) 0.02707(7) 0.40641(9) 0.0427(4) Uani 1 1 d . . .
N2 N 0.80295(16) 0.06160(8) 0.32527(10) 0.0360(4) Uani 1 1 d . . .
H2A H 0.7177 0.0453 0.2977 0.043 Uiso 1 1 calc R . .
C7 C 0.8278(2) 0.13851(10) 0.32414(13) 0.0347(5) Uani 1 1 d . . .
C8 C 0.9581(2) 0.16496(12) 0.31094(15) 0.0477(6) Uani 1 1 d . . .
H8A H 1.0303 0.1313 0.3050 0.057 Uiso 1 1 calc R . .
C9 C 0.9804(2) 0.23787(12) 0.30680(15) 0.0515(6) Uani 1 1 d . . .
H9A H 1.0689 0.2549 0.2983 0.062 Uiso 1 1 calc R . .
C10 C 0.8748(2) 0.28960(11) 0.31477(13) 0.0406(5) Uani 1 1 d . . .
C11 C 0.8948(3) 0.36622(12) 0.30937(16) 0.0529(6) Uani 1 1 d . . .
H11A H 0.9822 0.3842 0.3004 0.064 Uiso 1 1 calc R . .
C12 C 0.7909(3) 0.41477(12) 0.31672(15) 0.0554(7) Uani 1 1 d . . .
H12A H 0.8050 0.4660 0.3114 0.066 Uiso 1 1 calc R . .
C13 C 0.6632(2) 0.38904(12) 0.33209(14) 0.0479(6) Uani 1 1 d . . .
H13A H 0.5916 0.4231 0.3381 0.057 Uiso 1 1 calc R . .
C14 C 0.6404(2) 0.31537(11) 0.33860(12) 0.0381(5) Uani 1 1 d . . .
H14A H 0.5537 0.2990 0.3498 0.046 Uiso 1 1 calc R . .
C15 C 0.7440(2) 0.26316(10) 0.32896(12) 0.0333(5) Uani 1 1 d . . .
C16 C 0.72195(19) 0.18606(10) 0.33402(11) 0.0285(4) Uani 1 1 d . . .
C17 C 0.58945(19) 0.15650(9) 0.35431(11) 0.0280(4) Uani 1 1 d . . .
C18 C 0.5975(2) 0.13819(10) 0.43604(12) 0.0310(5) Uani 1 1 d . . .
C19 C 0.7243(2) 0.14951(11) 0.49929(13) 0.0409(5) Uani 1 1 d . . .
H19A H 0.8080 0.1696 0.4877 0.049 Uiso 1 1 calc R . .
C20 C 0.7286(3) 0.13211(13) 0.57628(14) 0.0526(6) Uani 1 1 d . . .
H20A H 0.8150 0.1402 0.6177 0.063 Uiso 1 1 calc R . .
C21 C 0.6074(3) 0.10238(13) 0.59545(14) 0.0525(6) Uani 1 1 d . . .
H21A H 0.6117 0.0907 0.6497 0.063 Uiso 1 1 calc R . .
C22 C 0.4831(2) 0.09016(12) 0.53632(14) 0.0453(6) Uani 1 1 d . . .
H22A H 0.4014 0.0697 0.5497 0.054 Uiso 1 1 calc R . .
C23 C 0.4742(2) 0.10759(10) 0.45542(12) 0.0333(5) Uani 1 1 d . . .
C24 C 0.3458(2) 0.09663(10) 0.39297(13) 0.0374(5) Uani 1 1 d . . .
H24A H 0.2630 0.0761 0.4051 0.045 Uiso 1 1 calc R . .
C25 C 0.3396(2) 0.11506(10) 0.31633(13) 0.0343(5) Uani 1 1 d . . .
H25A H 0.2522 0.1078 0.2753 0.041 Uiso 1 1 calc R . .
C26 C 0.46184(19) 0.14503(10) 0.29656(11) 0.0281(4) Uani 1 1 d . . .
N3 N 0.44668(16) 0.16062(8) 0.21330(9) 0.0303(4) Uani 1 1 d . . .
H3B H 0.4138 0.2037 0.1933 0.036 Uiso 1 1 calc R . .
C27 C 0.48259(19) 0.10949(10) 0.16553(12) 0.0307(5) Uani 1 1 d . . .
O2 O 0.54664(14) 0.05229(7) 0.19118(8) 0.0404(4) Uani 1 1 d . . .
C28 C 0.4351(2) 0.12537(10) 0.07762(12) 0.0336(5) Uani 1 1 d . . .
C29 C 0.4277(2) 0.19453(11) 0.04417(12) 0.0370(5) Uani 1 1 d . . .
H29A H 0.4581 0.2364 0.0773 0.044 Uiso 1 1 calc R . .
C30 C 0.3457(4) 0.08096(14) -0.05574(16) 0.0842(10) Uani 1 1 d . . .
H30A H 0.3196 0.0400 -0.0908 0.101 Uiso 1 1 calc R . .
N4 N 0.3345(3) 0.14723(10) -0.08841(12) 0.0616(6) Uani 1 1 d . . .
C32 C 0.3927(3) 0.06723(12) 0.02573(14) 0.0625(8) Uani 1 1 d . . .
H32A H 0.3956 0.0184 0.0457 0.075 Uiso 1 1 calc R . .
C31 C 0.3757(2) 0.20221(12) -0.03793(13) 0.0458(6) Uani 1 1 d . . .
H31A H 0.3691 0.2505 -0.0596 0.055 Uiso 1 1 calc R . .
O50 O 1.0569(4) 0.08096(19) 0.1367(3) 0.0620(10) Uiso 0.55 1 d PD A 1
C51 C 0.9148(7) 0.0542(4) 0.1273(5) 0.063(2) Uiso 0.55 1 d PD A 1
H51A H 0.8946 0.0124 0.0893 0.075 Uiso 0.55 1 calc PR A 1
H51B H 0.9017 0.0377 0.1796 0.075 Uiso 0.55 1 calc PR A 1
C52 C 0.8230(6) 0.1135(3) 0.0971(5) 0.0610(14) Uiso 0.55 1 d PD A 1
H52A H 0.7824 0.1336 0.1397 0.073 Uiso 0.55 1 calc PR A 1
H52B H 0.7417 0.0969 0.0520 0.073 Uiso 0.55 1 calc PR A 1
C53 C 0.9064(7) 0.1708(4) 0.0689(5) 0.073(2) Uiso 0.55 1 d PD A 1
H53A H 0.9201 0.2150 0.1036 0.088 Uiso 0.55 1 calc PR A 1
H53B H 0.8602 0.1850 0.0125 0.088 Uiso 0.55 1 calc PR A 1
C54 C 1.0514(6) 0.1289(3) 0.0772(4) 0.0676(18) Uiso 0.55 1 d PD A 1
H54A H 1.0511 0.1032 0.0267 0.081 Uiso 0.55 1 calc PR A 1
H54B H 1.1349 0.1631 0.0913 0.081 Uiso 0.55 1 calc PR A 1
O60 O 0.9939(15) 0.0806(6) 0.1533(6) 0.069(3) Uiso 0.20 1 d PD B 2
C61 C 1.0656(12) 0.0810(8) 0.0941(9) 0.049(3) Uiso 0.20 1 d PD B 2
H61A H 1.0830 0.0304 0.0778 0.059 Uiso 0.20 1 calc PR B 2
H61B H 1.1594 0.1071 0.1120 0.059 Uiso 0.20 1 calc PR B 2
C62 C 0.9538(15) 0.1247(8) 0.0211(8) 0.063(4) Uiso 0.20 1 d PD B 2
H62A H 0.9960 0.1724 0.0114 0.075 Uiso 0.20 1 calc PR B 2
H62B H 0.9337 0.0954 -0.0290 0.075 Uiso 0.20 1 calc PR B 2
C63 C 0.8172(14) 0.1369(10) 0.0457(8) 0.067(4) Uiso 0.20 1 d PD B 2
H63A H 0.7408 0.1016 0.0189 0.081 Uiso 0.20 1 calc PR B 2
H63B H 0.7806 0.1876 0.0335 0.081 Uiso 0.20 1 calc PR B 2
C64 C 0.867(2) 0.1235(13) 0.1352(11) 0.120(9) Uiso 0.20 1 d PD B 2
H64A H 0.8860 0.1710 0.1640 0.144 Uiso 0.20 1 calc PR B 2
H64B H 0.7899 0.0976 0.1530 0.144 Uiso 0.20 1 calc PR B 2
C74 C 0.8123(11) 0.0939(7) 0.0615(9) 0.069(4) Uiso 0.25 1 d PD C 3
H74A H 0.7441 0.1081 0.0930 0.082 Uiso 0.25 1 calc PR C 3
H74B H 0.7588 0.0696 0.0110 0.082 Uiso 0.25 1 calc PR C 3
C73 C 0.9073(11) 0.1634(5) 0.0451(7) 0.034(3) Uiso 0.25 1 d PD C 3
H73A H 0.8593 0.1877 -0.0065 0.041 Uiso 0.25 1 calc PR C 3
H73B H 0.9219 0.1999 0.0890 0.041 Uiso 0.25 1 calc PR C 3
C72 C 1.0330(12) 0.1334(5) 0.0424(9) 0.050(3) Uiso 0.25 1 d PD C 3
H72A H 1.1130 0.1496 0.0884 0.060 Uiso 0.25 1 calc PR C 3
H72B H 1.0570 0.1460 -0.0084 0.060 Uiso 0.25 1 calc PR C 3
O70 O 0.9364(11) 0.0467(5) 0.1102(6) 0.069(3) Uiso 0.25 1 d PD C 3
C71 C 1.0047(15) 0.0548(7) 0.0469(9) 0.100(4) Uiso 0.25 1 d PD C 3
H71A H 0.9404 0.0371 -0.0046 0.120 Uiso 0.25 1 calc PR C 3
H71B H 1.0963 0.0266 0.0588 0.120 Uiso 0.25 1 calc PR C 3
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
N1 C5 C1 124.02(19) . . ?
C5 C1 C2 118.74(18) . . ?
C3 C2 C1 118.12(17) . . ?
C3 C2 C6 122.76(17) . . ?
C1 C2 C6 119.11(16) . . ?
C2 C3 C4 118.88(18) . . ?
N1 C4 C3 123.90(19) . . ?
C4 N1 C5 116.25(17) . . ?
O1 C6 N2 123.94(17) . . ?
O1 C6 C2 121.04(17) . . ?
N2 C6 C2 115.01(16) . . ?
C6 N2 C7 125.24(16) . . ?
C16 C7 C8 121.18(18) . . ?
C16 C7 N2 119.03(17) . . ?
C8 C7 N2 119.77(18) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C10 121.43(19) . . ?
C11 C10 C9 122.5(2) . . ?
C11 C10 C15 119.0(2) . . ?
C9 C10 C15 118.50(18) . . ?
C12 C11 C10 121.2(2) . . ?
C11 C12 C13 119.9(2) . . ?
C14 C13 C12 120.7(2) . . ?
C13 C14 C15 121.0(2) . . ?
C14 C15 C10 118.09(18) . . ?
C14 C15 C16 122.23(18) . . ?
C10 C15 C16 119.68(18) . . ?
C7 C16 C15 118.97(17) . . ?
C7 C16 C17 119.96(16) . . ?
C15 C16 C17 120.98(16) . . ?
C26 C17 C18 118.93(17) . . ?
C26 C17 C16 121.94(17) . . ?
C18 C17 C16 119.11(16) . . ?
C19 C18 C23 118.07(18) . . ?
C19 C18 C17 122.39(18) . . ?
C23 C18 C17 119.54(17) . . ?
C20 C19 C18 121.1(2) . . ?
C19 C20 C21 120.9(2) . . ?
C22 C21 C20 120.0(2) . . ?
C21 C22 C23 120.8(2) . . ?
C22 C23 C24 122.06(19) . . ?
C22 C23 C18 119.07(18) . . ?
C24 C23 C18 118.85(18) . . ?
C25 C24 C23 120.78(19) . . ?
C24 C25 C26 120.69(18) . . ?
C17 C26 C25 121.21(18) . . ?
C17 C26 N3 122.01(17) . . ?
C25 C26 N3 116.75(16) . . ?
C27 N3 C26 120.20(15) . . ?
O2 C27 N3 123.29(18) . . ?
O2 C27 C28 121.17(17) . . ?
N3 C27 C28 115.51(16) . . ?
C32 C28 C29 117.1(2) . . ?
C32 C28 C27 118.04(18) . . ?
C29 C28 C27 124.80(18) . . ?
C31 C29 C28 119.17(19) . . ?
N4 C30 C32 124.5(2) . . ?
C31 N4 C30 115.8(2) . . ?
C28 C32 C30 118.9(2) . . ?
N4 C31 C29 124.5(2) . . ?
C54 O50 C51 107.3(4) . . ?
C52 C51 O50 105.4(5) . . ?
C51 C52 C53 109.0(5) . . ?
C52 C53 C54 100.0(5) . . ?
O50 C54 C53 103.9(5) . . ?
C61 O60 C64 113.9(11) . . ?
O60 C61 C62 102.8(9) . . ?
C63 C62 C61 107.3(10) . . ?
C62 C63 C64 101.9(10) . . ?
O60 C64 C63 109.5(13) . . ?
O70 C74 C73 98.3(7) . . ?
C72 C73 C74 104.0(8) . . ?
C73 C72 C71 102.5(9) . . ?
C71 O70 C74 88.3(9) . . ?
O70 C71 C72 105.8(11) . . ?
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
C5 N1 1.344(3) . ?
C5 C1 1.376(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.378(3) . ?
C2 C6 1.496(3) . ?
C3 C4 1.387(3) . ?
C4 N1 1.328(3) . ?
C6 O1 1.223(2) . ?
C6 N2 1.348(2) . ?
N2 C7 1.421(2) . ?
C7 C16 1.378(3) . ?
C7 C8 1.413(3) . ?
C8 C9 1.349(3) . ?
C9 C10 1.415(3) . ?
C10 C11 1.414(3) . ?
C10 C15 1.424(3) . ?
C11 C12 1.362(3) . ?
C12 C13 1.400(3) . ?
C13 C14 1.368(3) . ?
C14 C15 1.416(3) . ?
C15 C16 1.425(3) . ?
C16 C17 1.504(3) . ?
C17 C26 1.371(3) . ?
C17 C18 1.431(3) . ?
C18 C19 1.414(3) . ?
C18 C23 1.425(3) . ?
C19 C20 1.356(3) . ?
C20 C21 1.399(3) . ?
C21 C22 1.363(3) . ?
C22 C23 1.412(3) . ?
C23 C24 1.416(3) . ?
C24 C25 1.351(3) . ?
C25 C26 1.414(3) . ?
C26 N3 1.434(3) . ?
N3 C27 1.348(2) . ?
C27 O2 1.229(2) . ?
C27 C28 1.491(3) . ?
C28 C32 1.375(3) . ?
C28 C29 1.378(3) . ?
C29 C31 1.378(3) . ?
C30 N4 1.323(3) . ?
C30 C32 1.380(3) . ?
N4 C31 1.316(3) . ?
O50 C54 1.338(7) . ?
O50 C51 1.414(7) . ?
C51 C52 1.403(8) . ?
C52 C53 1.472(8) . ?
C53 C54 1.557(8) . ?
O60 C61 1.376(14) . ?
O60 C64 1.409(16) . ?
C61 C62 1.626(14) . ?
C62 C63 1.497(15) . ?
C63 C64 1.509(17) . ?
C74 O70 1.524(13) . ?
C74 C73 1.626(13) . ?
C73 C72 1.334(13) . ?
C72 C71 1.461(14) . ?
O70 C71 1.423(13) . ?
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
N2 H2A O2 0.88 2.11 2.893(2) 147.3 .
N3 H3B N1 0.88 2.19 3.008(2) 154.5 2_655
