#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:32:36 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178953 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/82/4118269.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_4118269
loop_
_publ_author_name
'Ming Li'
'A. Dieter Schlüter'
'Junji Sakamoto'
_publ_section_title
;
 Solid-State Photopolymerization of a Shape-Persistent Macrocycle with Two
 1,8-Diazaanthracene Units in a Single Crystal
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11721
_journal_page_last               11725
_journal_paper_doi               10.1021/ja3038905
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C188 H68 Cl28 N12 O5'
_chemical_formula_weight         3567.14
_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                 131.806(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.3446(8)
_cell_length_b                   29.3622(16)
_cell_length_c                   16.6429(6)
_cell_measurement_temperature    100(2)
_cell_volume                     8139.2(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            67156
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    1.061
_exptl_absorpt_correction_T_max  0.8833
_exptl_absorpt_correction_T_min  0.8486
_exptl_crystal_density_diffrn    2.911
_exptl_crystal_F_000             7184
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.746
_refine_diff_density_min         -1.791
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.756
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         9374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.756
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.1203
_refine_ls_shift/su_max          14.018
_refine_ls_shift/su_mean         0.152
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3910
_refine_ls_wR_factor_ref         0.4261
_reflns_number_gt                6595
_reflns_number_total             9374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3038905_si_005.cif
_cod_data_source_block           mo_sc210312_0ma
_cod_original_cell_volume        8139.2(6)
_cod_database_code               4118269
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl00 Cl 0.52511(10) 0.40114(6) 0.64696(19) 0.0927(8) Uani 1 1 d . . .
Cl02 Cl 0.59943(10) 0.45129(6) 0.8444(2) 0.1226(12) Uani 1 1 d . . .
C0AA C 0.8089(3) 0.84423(14) 0.4572(4) 0.0394(11) Uani 1 1 d . . .
Cl2 Cl 0.3827(6) 0.6113(3) 0.5229(9) 0.093(3) Uani 0.243(5) 1 d P A 2
Cl3 Cl 0.4208(3) 0.57944(15) 0.5775(3) 0.1293(16) Uani 0.757(5) 1 d P A 1
Cl1S Cl 0.3924(3) 0.57457(14) 0.7181(4) 0.1260(15) Uani 0.757(5) 1 d P A 1
O1 O 0.9947(2) 0.19736(10) 0.9075(3) 0.0444(9) Uani 1 1 d . . .
Cl2S Cl 0.4898(4) 0.5287(3) 0.5570(6) 0.076(2) Uani 0.243(5) 1 d P A 2
C1 C 0.9508(4) 0.17404(19) 0.9270(6) 0.0629(17) Uani 1 1 d . . .
C2 C 0.9985(3) 0.24363(13) 0.9149(3) 0.0297(9) Uani 1 1 d . . .
C3 C 1.0410(3) 0.26523(14) 0.8923(4) 0.0398(11) Uani 1 1 d . . .
C4 C 1.0476(3) 0.31197(14) 0.8986(4) 0.0397(11) Uani 1 1 d . . .
C5 C 1.0128(3) 0.33850(13) 0.9271(3) 0.0279(9) Uani 1 1 d . . .
C6 C 1.0213(3) 0.38935(12) 0.9325(3) 0.0263(9) Uani 1 1 d . . .
C7 C 0.9623(2) 0.41572(13) 0.8424(3) 0.0257(8) Uani 1 1 d . . .
C8 C 0.9756(2) 0.46281(12) 0.8481(3) 0.0225(8) Uani 1 1 d . . .
C9 C 0.9173(2) 0.49218(13) 0.7533(3) 0.0236(8) Uani 1 1 d . . .
C10 C 0.9279(2) 0.53889(13) 0.7639(3) 0.0281(9) Uani 1 1 d . . .
C11 C 0.8758(2) 0.56693(14) 0.6731(3) 0.0285(9) Uani 1 1 d . . .
C12 C 0.8874(2) 0.61506(14) 0.6819(3) 0.0308(9) Uani 1 1 d . . .
C13 C 0.8946(2) 0.65588(14) 0.6863(3) 0.0295(9) Uani 1 1 d . . .
C14 C 0.8955(2) 0.70403(14) 0.6779(3) 0.0276(9) Uani 1 1 d . . .
C15 C 0.8559(2) 0.72333(12) 0.5737(3) 0.0251(8) Uani 1 1 d . . .
C16 C 0.8193(2) 0.69666(13) 0.4828(3) 0.0252(8) Uani 1 1 d . . .
C17 C 0.7788(2) 0.71676(13) 0.3829(3) 0.0270(9) Uani 1 1 d . . .
C18 C 0.7379(3) 0.68976(14) 0.2860(4) 0.0334(10) Uani 1 1 d . . .
C19 C 0.7441(3) 0.64145(15) 0.2921(3) 0.0343(10) Uani 1 1 d . . .
C20 C 1.2497(3) 0.60077(15) 1.2055(3) 0.0358(10) Uani 1 1 d . . .
C21 C 1.2424(3) 0.55208(14) 1.2058(3) 0.0328(9) Uani 1 1 d . . .
C22 C 1.1731(3) 0.52954(14) 1.1174(3) 0.0342(10) Uani 1 1 d . . .
C23 C 1.1680(3) 0.48231(13) 1.1169(3) 0.0271(9) Uani 1 1 d . . .
C24 C 1.0965(3) 0.45786(12) 1.0228(3) 0.0259(8) Uani 1 1 d . . .
C25 C 1.0892(3) 0.41055(13) 1.0244(3) 0.0316(9) Uani 1 1 d . . .
C26 C 0.9701(2) 0.31665(13) 0.9490(3) 0.0279(9) Uani 1 1 d . . .
C27 C 0.9629(3) 0.26931(14) 0.9434(3) 0.0299(9) Uani 1 1 d . . .
C28 C 1.3052(3) 0.52733(16) 1.2955(4) 0.0444(12) Uani 1 1 d . . .
C29 C 1.2998(3) 0.48026(18) 1.2941(4) 0.0546(15) Uani 1 1 d . . .
C30 C 1.2325(3) 0.45770(16) 1.2057(4) 0.0404(11) Uani 1 1 d . . .
C31 C 1.2279(4) 0.4060(2) 1.1969(7) 0.106(4) Uani 1 1 d . . .
C32 C 1.1533(5) 0.38475(16) 1.1259(4) 0.088(3) Uani 1 1 d . . .
C33 C 0.6966(3) 0.71254(17) 0.1898(4) 0.0448(12) Uani 1 1 d . . .
C34 C 0.6980(4) 0.76108(17) 0.1914(4) 0.0475(13) Uani 1 1 d . . .
C35E C 0.5405(3) 0.40361(18) 0.7684(7) 0.088(3) Uani 1 1 d . . .
N35 N 0.7347(3) 0.78641(13) 0.2749(3) 0.0393(9) Uani 1 1 d . . .
C36 C 0.7753(2) 0.76546(13) 0.3738(4) 0.0299(9) Uani 1 1 d . . .
C37 C 0.8131(2) 0.79263(13) 0.4646(4) 0.0291(9) Uani 1 1 d . . .
C38 C 0.8539(2) 0.77206(13) 0.5654(3) 0.0268(9) Uani 1 1 d . . .
N39 N 0.89085(19) 0.80004(12) 0.6549(3) 0.0340(9) Uani 1 1 d . . .
C40 C 0.9262(3) 0.78000(16) 0.7469(4) 0.0397(11) Uani 1 1 d . . .
C41 C 0.9302(3) 0.73283(16) 0.7637(4) 0.0378(11) Uani 1 1 d . . .
C42 C 0.8855(3) 0.39617(15) 0.7432(4) 0.0390(11) Uani 1 1 d . . .
C43 C 0.8522(3) 0.42143(15) 0.6423(4) 0.0427(12) Uani 1 1 d . . .
C44 C 0.8551(2) 0.47263(13) 0.6536(3) 0.0273(8) Uani 1 1 d . . .
C45 C 0.8019(3) 0.50094(15) 0.5639(4) 0.0358(10) Uani 1 1 d . . .
C46 C 0.8122(3) 0.54752(15) 0.5730(4) 0.0330(9) Uani 1 1 d . . .
N47 N 1.0405(2) 0.48355(10) 0.9361(3) 0.0237(7) Uani 1 1 d . . .
C48 C 0.1771(7) 0.7369(4) 0.3496(11) 0.116(4) Uani 1 1 d . . .
C49 C 0.2790(9) 0.7233(6) 0.5543(14) 0.140(5) Uani 1 1 d . . .
C50 C 0.2269(5) 0.7209(4) 0.4369(7) 0.079(2) Uani 1 1 d . . .
C51 C 0.1776(8) 0.8004(6) 0.3662(10) 0.136(5) Uani 1 1 d . . .
C52 C 0.2726(11) 0.6894(5) 0.5130(15) 0.160(7) Uani 1 1 d . . .
C1A C 0.4420(18) 0.5824(9) 0.746(2) 0.0771(17) Uiso 0.243(5) 1 d P A 2
C1B C 0.4708(4) 0.5679(3) 0.7201(6) 0.0771(17) Uiso 0.757(5) 1 d P . 1
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
C2 O1 C1 118.6(4) . .
O1 C2 C3 116.5(4) . .
O1 C2 C27 123.7(4) . .
C3 C2 C27 119.7(4) . .
C4 C3 C2 119.7(4) . .
C3 C4 C5 121.9(4) . .
C26 C5 C4 118.1(4) . .
C26 C5 C6 121.8(3) . .
C4 C5 C6 120.1(4) . .
C25 C6 C7 119.3(3) . .
C25 C6 C5 120.9(3) . .
C7 C6 C5 119.7(4) . .
C8 C7 C6 117.9(4) . .
C8 C7 C42 119.3(3) . .
C6 C7 C42 122.8(4) . .
N47 C8 C7 123.3(3) . .
N47 C8 C9 116.3(3) . .
C7 C8 C9 120.4(4) . .
C10 C9 C44 120.7(3) . .
C10 C9 C8 119.2(4) . .
C44 C9 C8 120.0(3) . .
C9 C10 C11 119.7(4) . .
C46 C11 C10 119.8(4) . .
C46 C11 C12 119.7(3) . .
C10 C11 C12 120.5(4) . .
C13 C12 C11 177.9(5) . .
C12 C13 C14 173.2(4) . .
C41 C14 C13 123.1(4) . .
C41 C14 C15 118.6(4) . .
C13 C14 C15 118.2(4) . .
C16 C15 C14 122.3(3) . .
C16 C15 C38 120.0(3) . .
C14 C15 C38 117.7(4) . .
C15 C16 C17 120.4(3) . .
C16 C17 C36 119.8(4) . .
C16 C17 C18 121.6(3) . .
C36 C17 C18 118.5(3) . .
C33 C18 C19 121.7(4) . .
C33 C18 C17 117.7(4) . .
C19 C18 C17 120.5(4) . .
C20 C19 C18 177.0(5) 2_756 .
C19 C20 C21 177.9(4) 2_756 .
C28 C21 C22 119.9(4) . .
C28 C21 C20 119.2(4) . .
C22 C21 C20 120.9(4) . .
C23 C22 C21 120.4(4) . .
C22 C23 C30 119.2(4) . .
C22 C23 C24 121.1(4) . .
C30 C23 C24 119.7(4) . .
N47 C24 C25 122.6(4) . .
N47 C24 C23 116.1(3) . .
C25 C24 C23 121.3(3) . .
C6 C25 C24 118.6(3) . .
C6 C25 C32 122.3(4) . .
C24 C25 C32 119.1(4) . .
C5 C26 C27 120.9(4) . .
C2 C27 C26 119.7(4) . .
C29 C28 C21 119.3(4) . .
C28 C29 C30 121.0(4) . .
C23 C30 C29 120.1(4) . .
C23 C30 C31 117.4(4) . .
C29 C30 C31 122.4(4) . .
C32 C31 C30 119.6(5) . .
C31 C32 C25 115.7(5) . .
C18 C33 C34 118.4(5) . .
N35 C34 C33 126.2(4) . .
C35E C35E Cl02 115.0(6) 2_656 .
C35E C35E Cl00 105.6(8) 2_656 .
Cl02 C35E Cl00 109.3(4) . .
C34 N35 C36 118.1(4) . .
N35 C36 C37 118.6(4) . .
N35 C36 C17 121.0(4) . .
C37 C36 C17 120.4(4) . .
C36 C37 C38 119.5(3) . .
C36 C37 C0AA 121.7(4) . .
C38 C37 C0AA 118.8(4) . .
N39 C38 C37 118.3(3) . .
N39 C38 C15 121.8(4) . .
C37 C38 C15 119.9(4) . .
C40 N39 C38 117.0(4) . .
N39 C40 C41 125.9(4) . .
C14 C41 C40 119.0(4) . .
C7 C42 C43 113.2(4) . .
C42 C43 C44 113.8(4) . .
C9 C44 C45 119.2(4) . .
C9 C44 C43 118.9(3) . .
C45 C44 C43 121.5(4) . .
C46 C45 C44 120.7(4) . .
C45 C46 C11 119.8(4) . .
C8 N47 C24 118.3(3) . .
C50 C48 C49 68.4(11) . 7_566
C50 C48 C51 107.6(11) . .
C49 C48 C51 39.2(7) 7_566 .
C51 C49 C52 81.2(19) 7_566 .
C51 C49 C50 140.8(18) 7_566 .
C52 C49 C50 59.7(12) . .
C51 C49 C48 80.0(13) 7_566 7_566
C52 C49 C48 158(2) . 7_566
C50 C49 C48 138.4(14) . 7_566
C51 C49 C50 121.7(15) 7_566 7_566
C52 C49 C50 155.9(18) . 7_566
C50 C49 C50 97.3(12) . 7_566
C48 C49 C50 41.8(6) 7_566 7_566
C48 C50 C52 159.2(13) . .
C48 C50 C49 151.1(14) . .
C52 C50 C49 48.8(8) . .
C48 C50 C49 69.8(11) . 7_566
C52 C50 C49 131.0(10) . 7_566
C49 C50 C49 82.7(12) . 7_566
C49 C51 C52 48.1(10) 7_566 7_566
C49 C51 C48 60.8(13) 7_566 .
C52 C51 C48 108.1(12) 7_566 .
C49 C52 C50 71.5(15) . .
C49 C52 C51 50.8(12) . 7_566
C50 C52 C51 122.3(14) . 7_566
C1B C1B Cl1S 131.3(11) 2_656 .
C1B C1B Cl3 123.9(11) 2_656 .
Cl1S C1B Cl3 102.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl00 C35E 1.812(11) .
Cl02 C35E 1.752(6) .
C0AA C37 1.518(5) .
Cl3 C1B 1.860(9) .
Cl1S C1B 1.741(9) .
O1 C2 1.362(5) .
O1 C1 1.401(7) .
C2 C3 1.384(6) .
C2 C27 1.391(6) .
C3 C4 1.377(6) .
C4 C5 1.389(6) .
C5 C26 1.385(6) .
C5 C6 1.500(5) .
C6 C25 1.391(6) .
C6 C7 1.397(5) .
C7 C8 1.404(5) .
C7 C42 1.492(6) .
C8 N47 1.337(5) .
C8 C9 1.479(5) .
C9 C10 1.383(5) .
C9 C44 1.393(6) .
C10 C11 1.404(5) .
C11 C46 1.401(6) .
C11 C12 1.426(6) .
C12 C13 1.205(6) .
C13 C14 1.422(6) .
C14 C41 1.371(6) .
C14 C15 1.437(5) .
C15 C16 1.386(6) .
C15 C38 1.435(5) .
C16 C17 1.388(5) .
C17 C36 1.435(5) .
C17 C18 1.449(6) .
C18 C33 1.376(6) .
C18 C19 1.422(6) .
C19 C20 1.200(6) 2_756
C20 C19 1.200(6) 2_756
C20 C21 1.440(6) .
C21 C28 1.390(6) .
C21 C22 1.402(6) .
C22 C23 1.391(5) .
C23 C30 1.394(6) .
C23 C24 1.477(6) .
C24 N47 1.346(5) .
C24 C25 1.401(5) .
C25 C32 1.501(6) .
C26 C27 1.395(5) .
C28 C29 1.386(7) .
C29 C30 1.384(7) .
C30 C31 1.523(7) .
C31 C32 1.393(9) .
C33 C34 1.425(7) .
C34 N35 1.280(7) .
C35E C35E 1.476(14) 2_656
N35 C36 1.386(5) .
C36 C37 1.390(6) .
C37 C38 1.404(6) .
C38 N39 1.392(6) .
N39 C40 1.305(6) .
C40 C41 1.404(6) .
C42 C43 1.503(7) .
C43 C44 1.511(6) .
C44 C45 1.402(6) .
C45 C46 1.378(6) .
C48 C50 1.188(14) .
C48 C49 1.67(2) 7_566
C48 C51 1.89(2) .
C49 C51 1.21(2) 7_566
C49 C52 1.162(17) .
C49 C50 1.465(19) .
C49 C48 1.67(2) 7_566
C49 C50 1.658(18) 7_566
C50 C52 1.333(19) .
C50 C49 1.657(18) 7_566
C51 C49 1.21(2) 7_566
C51 C52 1.54(2) 7_566
C52 C51 1.54(2) 7_566
C1B C1B 0.979(14) 2_656
