#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:25:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180078 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/24/7052448.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_7052448
loop_
_publ_author_name
'Heidi Mansikkamäki'
'Christoph A. Schalley'
'Maija Nissinen'
'Kari Rissanen'
_publ_section_title
;
 Weak interactions between resorcinarenes and diquaternary alkyl
 ammonium cations
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              116
_journal_paper_doi               10.1039/b415401k
_journal_volume                  29
_journal_year                    2005
_chemical_formula_moiety         C40H48O8*C8H18N2Cl2*2CH4O
_chemical_formula_sum            'C50 H74 Cl2 N2 O10'
_chemical_formula_weight         934.01
_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                99.3590(10)
_cell_angle_beta                 91.1830(10)
_cell_angle_gamma                98.7800(10)
_cell_formula_units_Z            2
_cell_length_a                   11.3877(2)
_cell_length_b                   12.5699(3)
_cell_length_c                   17.5983(4)
_cell_measurement_reflns_used    13449
_cell_measurement_temperature    173(2)
_cell_volume                     2453.73(9)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       Collect
_computing_data_reduction        DENZO-SMN
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 1 deg.'
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13447
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         8606
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0605
_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)+(0.0499P)²+3.6908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                5747
_reflns_number_total             8606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b415401k.txt
_cod_data_source_block           Complex4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_database_code               7052448
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6437(3) 0.9009(2) 0.24430(18) 0.0187(7) Uani 1 1 d . . .
C2 C 0.5860(2) 0.7936(2) 0.22315(18) 0.0183(7) Uani 1 1 d . . .
H2 H 0.5945 0.7570 0.1724 0.022 Uiso 1 1 calc R . .
C3 C 0.5165(2) 0.7373(2) 0.27255(18) 0.0164(7) Uani 1 1 d . . .
C4 C 0.5062(3) 0.7926(2) 0.34678(18) 0.0192(7) Uani 1 1 d . . .
O4 O 0.44062(19) 0.73627(18) 0.39644(13) 0.0251(5) Uani 1 1 d D . .
H4 H 0.450(3) 0.771(3) 0.4410(13) 0.038 Uiso 1 1 d D . .
C5 C 0.5611(3) 0.9001(3) 0.37015(19) 0.0226(7) Uani 1 1 d . . .
H5 H 0.5524 0.9368 0.4208 0.027 Uiso 1 1 calc R . .
C6 C 0.6288(3) 0.9532(2) 0.31867(19) 0.0203(7) Uani 1 1 d . . .
O6 O 0.6842(2) 1.05992(18) 0.34012(14) 0.0301(6) Uani 1 1 d D . .
H6 H 0.638(3) 1.093(3) 0.369(2) 0.045 Uiso 1 1 d D . .
C7 C 0.4554(3) 0.6189(2) 0.24932(18) 0.0180(7) Uani 1 1 d . . .
H7 H 0.3808 0.6113 0.2783 0.022 Uiso 1 1 calc R . .
C8 C 0.5323(3) 0.5408(2) 0.27587(18) 0.0180(7) Uani 1 1 d . . .
C9 C 0.6269(3) 0.5123(2) 0.23195(18) 0.0180(7) Uani 1 1 d . . .
H9 H 0.6443 0.5465 0.1883 0.022 Uiso 1 1 calc R . .
C10 C 0.6971(2) 0.4367(2) 0.24841(18) 0.0177(7) Uani 1 1 d . . .
C11 C 0.6729(3) 0.3909(2) 0.31434(19) 0.0198(7) Uani 1 1 d . . .
O11 O 0.7429(2) 0.31729(18) 0.33265(14) 0.0261(5) Uani 1 1 d D . .
H11 H 0.748(3) 0.320(3) 0.3798(11) 0.039 Uiso 1 1 d D . .
C12 C 0.5816(3) 0.4188(2) 0.36097(19) 0.0213(7) Uani 1 1 d . . .
H12 H 0.5670 0.3873 0.4061 0.026 Uiso 1 1 calc R . .
C13 C 0.5114(3) 0.4930(2) 0.34163(18) 0.0189(7) Uani 1 1 d . . .
O13 O 0.4219(2) 0.51389(18) 0.39030(14) 0.0283(6) Uani 1 1 d D . .
H13 H 0.412(3) 0.5791(17) 0.394(2) 0.042 Uiso 1 1 d D . .
C14 C 0.7931(3) 0.4035(2) 0.19378(18) 0.0193(7) Uani 1 1 d . . .
H14 H 0.8153 0.3349 0.2075 0.023 Uiso 1 1 calc R . .
C15 C 0.9053(3) 0.4891(2) 0.20641(18) 0.0189(7) Uani 1 1 d . . .
C17 C 1.0309(3) 0.6490(2) 0.17074(18) 0.0191(7) Uani 1 1 d . . .
C16 C 0.9306(3) 0.5684(2) 0.16024(18) 0.0185(7) Uani 1 1 d . . .
H16 H 0.8759 0.5677 0.1186 0.022 Uiso 1 1 calc R . .
C18 C 1.1106(3) 0.6479(3) 0.23221(19) 0.0220(7) Uani 1 1 d . . .
O18 O 1.21304(19) 0.72133(19) 0.25013(14) 0.0294(6) Uani 1 1 d D . .
H18 H 1.212(3) 0.776(2) 0.228(2) 0.044 Uiso 1 1 d D . .
C19 C 1.0890(3) 0.5693(3) 0.27988(19) 0.0235(7) Uani 1 1 d . . .
H19 H 1.1442 0.5690 0.3210 0.028 Uiso 1 1 calc R . .
C20 C 0.9873(3) 0.4916(3) 0.26742(19) 0.0219(7) Uani 1 1 d . . .
O20 O 0.9724(2) 0.42021(19) 0.31885(14) 0.0313(6) Uani 1 1 d D . .
H20 H 0.903(2) 0.385(3) 0.314(2) 0.047 Uiso 1 1 d D . .
C21 C 1.0519(3) 0.7389(2) 0.12194(18) 0.0196(7) Uani 1 1 d . . .
H21 H 1.1397 0.7555 0.1165 0.023 Uiso 1 1 calc R . .
C22 C 1.0133(3) 0.8433(2) 0.16429(18) 0.0188(7) Uani 1 1 d . . .
C23 C 0.8941(3) 0.8562(2) 0.16568(18) 0.0186(7) Uani 1 1 d . . .
H23 H 0.8371 0.7967 0.1410 0.022 Uiso 1 1 calc R . .
C24 C 0.8524(3) 0.9499(2) 0.20070(18) 0.0190(7) Uani 1 1 d . . .
C25 C 0.9368(3) 1.0326(2) 0.24121(18) 0.0227(7) Uani 1 1 d . . .
O25 O 0.9091(2) 1.12862(19) 0.28124(16) 0.0386(7) Uani 1 1 d D . .
H25 H 0.8374(19) 1.117(3) 0.291(3) 0.058 Uiso 1 1 d D . .
C26 C 1.0566(3) 1.0236(3) 0.24177(19) 0.0238(7) Uani 1 1 d . . .
H26 H 1.1131 1.0814 0.2689 0.029 Uiso 1 1 calc R . .
C27 C 1.0946(3) 0.9308(3) 0.20311(18) 0.0210(7) Uani 1 1 d . . .
O27 O 1.21334(18) 0.91921(18) 0.20243(14) 0.0264(5) Uani 1 1 d D . .
H27 H 1.254(3) 0.974(2) 0.2288(19) 0.040 Uiso 1 1 d D . .
C28 C 0.7214(3) 0.9606(3) 0.18975(18) 0.0213(7) Uani 1 1 d . . .
H28 H 0.7161 1.0399 0.2046 0.026 Uiso 1 1 calc R . .
C29 C 0.4181(3) 0.5881(2) 0.16386(19) 0.0223(7) Uani 1 1 d . . .
H29A H 0.4903 0.5930 0.1334 0.027 Uiso 1 1 calc R . .
H29B H 0.3699 0.6418 0.1498 0.027 Uiso 1 1 calc R . .
C32 C 0.7444(3) 0.3763(3) 0.10978(19) 0.0227(7) Uani 1 1 d . . .
H32A H 0.7177 0.4418 0.0951 0.027 Uiso 1 1 calc R . .
H32B H 0.8094 0.3577 0.0760 0.027 Uiso 1 1 calc R . .
C30 C 0.3464(3) 0.4737(3) 0.1418(2) 0.0326(9) Uani 1 1 d . . .
H30A H 0.3928 0.4200 0.1578 0.039 Uiso 1 1 calc R . .
H30B H 0.2719 0.4697 0.1699 0.039 Uiso 1 1 calc R . .
C31 C 0.3159(4) 0.4438(4) 0.0558(2) 0.0598(13) Uani 1 1 d . . .
H31A H 0.2775 0.3673 0.0437 0.090 Uiso 1 1 calc R . .
H31B H 0.3888 0.4536 0.0274 0.090 Uiso 1 1 calc R . .
H31C H 0.2615 0.4909 0.0408 0.090 Uiso 1 1 calc R . .
C33 C 0.6412(3) 0.2818(3) 0.0960(2) 0.0313(8) Uani 1 1 d . . .
H33A H 0.6661 0.2176 0.1138 0.038 Uiso 1 1 calc R . .
H33B H 0.5740 0.3023 0.1270 0.038 Uiso 1 1 calc R . .
C34 C 0.5993(2) 0.2510(2) 0.01182(14) 0.0471(11) Uani 1 1 d . . .
H34A H 0.5359 0.1876 0.0055 0.071 Uiso 1 1 calc R . .
H34B H 0.6660 0.2329 -0.0194 0.071 Uiso 1 1 calc R . .
H34C H 0.5689 0.3126 -0.0051 0.071 Uiso 1 1 calc R . .
C35 C 0.9944(2) 0.7066(2) 0.03999(14) 0.0221(7) Uani 1 1 d R . .
H35A H 1.0173 0.6364 0.0159 0.026 Uiso 1 1 calc R . .
H35B H 0.9068 0.6953 0.0433 0.026 Uiso 1 1 calc R . .
C36 C 1.0302(3) 0.7918(3) -0.01128(19) 0.0284(8) Uani 1 1 d . . .
H36A H 1.0094 0.8625 0.0137 0.034 Uiso 1 1 calc R . .
H36B H 1.1176 0.8016 -0.0156 0.034 Uiso 1 1 calc R . .
C37 C 0.9713(4) 0.7623(3) -0.0920(2) 0.0414(10) Uani 1 1 d . . .
H37A H 1.0047 0.8161 -0.1234 0.062 Uiso 1 1 calc R . .
H37B H 0.8854 0.7623 -0.0888 0.062 Uiso 1 1 calc R . .
H37C H 0.9857 0.6896 -0.1156 0.062 Uiso 1 1 calc R . .
C38 C 0.6767(3) 0.9277(3) 0.10512(18) 0.0224(7) Uani 1 1 d . . .
H38A H 0.6783 0.8487 0.0888 0.027 Uiso 1 1 calc R . .
H38B H 0.5930 0.9394 0.1008 0.027 Uiso 1 1 calc R . .
C39 C 0.7493(3) 0.9908(3) 0.0506(2) 0.0317(8) Uani 1 1 d . . .
H39A H 0.7504 1.0699 0.0679 0.038 Uiso 1 1 calc R . .
H39B H 0.8323 0.9766 0.0531 0.038 Uiso 1 1 calc R . .
C40 C 0.7003(4) 0.9599(4) -0.0321(2) 0.0473(11) Uani 1 1 d . . .
H40A H 0.7500 1.0024 -0.0649 0.071 Uiso 1 1 calc R . .
H40B H 0.6187 0.9755 -0.0351 0.071 Uiso 1 1 calc R . .
H40C H 0.7003 0.8818 -0.0499 0.071 Uiso 1 1 calc R . .
Cl1 Cl 0.51369(7) 0.84267(7) 0.56332(5) 0.0299(2) Uani 1 1 d . . .
Cl2 Cl 0.79052(8) 0.36742(9) 0.50439(6) 0.0424(3) Uani 1 1 d . . .
N2 N 0.8527(2) 0.7350(2) 0.42099(16) 0.0264(7) Uani 1 1 d . . .
N1 N 0.8197(2) 0.7012(2) 0.55845(16) 0.0244(6) Uani 1 1 d . . .
C50 C 0.8718(3) 0.7551(3) 0.3402(2) 0.0397(9) Uani 1 1 d . . .
H50A H 0.9513 0.7968 0.3377 0.060 Uiso 1 1 calc R . .
H50B H 0.8117 0.7965 0.3247 0.060 Uiso 1 1 calc R . .
H50C H 0.8650 0.6850 0.3052 0.060 Uiso 1 1 calc R . .
C51 C 0.7999(3) 0.6823(3) 0.6393(2) 0.0338(9) Uani 1 1 d . . .
H51A H 0.7379 0.7228 0.6609 0.051 Uiso 1 1 calc R . .
H51B H 0.8740 0.7075 0.6708 0.051 Uiso 1 1 calc R . .
H51C H 0.7748 0.6041 0.6393 0.051 Uiso 1 1 calc R . .
C52 C 0.8382(3) 0.8216(3) 0.5558(2) 0.0360(9) Uani 1 1 d . . .
H52A H 0.8997 0.8603 0.5955 0.043 Uiso 1 1 calc R . .
H52B H 0.7632 0.8507 0.5670 0.043 Uiso 1 1 calc R . .
C54 C 0.9281(3) 0.6566(3) 0.5284(2) 0.0378(9) Uani 1 1 d . . .
H54A H 0.9244 0.5804 0.5373 0.045 Uiso 1 1 calc R . .
H54B H 1.0006 0.7008 0.5559 0.045 Uiso 1 1 calc R . .
C55 C 0.9330(4) 0.6603(4) 0.4427(2) 0.0455(11) Uani 1 1 d . . .
H55A H 1.0155 0.6864 0.4301 0.055 Uiso 1 1 calc R . .
H55B H 0.9080 0.5860 0.4130 0.055 Uiso 1 1 calc R . .
C53 C 0.8772(4) 0.8413(3) 0.4761(2) 0.0446(10) Uani 1 1 d . . .
H53A H 0.8330 0.8953 0.4582 0.053 Uiso 1 1 calc R . .
H53B H 0.9632 0.8708 0.4785 0.053 Uiso 1 1 calc R . .
C56 C 0.7143(3) 0.6481(3) 0.5063(2) 0.0318(9) Uani 1 1 d . . .
H56A H 0.6405 0.6679 0.5295 0.038 Uiso 1 1 calc R . .
H56B H 0.7088 0.5677 0.4992 0.038 Uiso 1 1 calc R . .
C57 C 0.7277(3) 0.6862(3) 0.4288(2) 0.0410(10) Uani 1 1 d . . .
H57A H 0.7040 0.6234 0.3867 0.049 Uiso 1 1 calc R . .
H57B H 0.6749 0.7409 0.4246 0.049 Uiso 1 1 calc R . .
O1M O 0.8321(3) 0.1189(5) 0.5197(3) 0.1225(18) Uani 1 1 d D . .
H1M H 0.7881 0.1448 0.4909 0.184 Uiso 1 1 calc RD . .
C2M C 0.7714(4) 0.0963(4) 0.5844(3) 0.0631(13) Uani 1 1 d . . .
H2MA H 0.7721 0.1642 0.6209 0.095 Uiso 1 1 calc R . .
H2MB H 0.8104 0.0455 0.6090 0.095 Uiso 1 1 calc R . .
H2MC H 0.6891 0.0632 0.5689 0.095 Uiso 1 1 calc R . .
O3M O 1.3552(2) 1.0957(2) 0.27706(15) 0.0385(6) Uani 1 1 d D . .
H3M H 1.390(4) 1.100(4) 0.3199(15) 0.058 Uiso 1 1 d D . .
C4M C 1.4386(4) 1.1471(4) 0.2303(2) 0.0558(13) Uani 1 1 d . . .
H4MA H 1.4838 1.0931 0.2035 0.084 Uiso 1 1 calc R . .
H4MB H 1.4933 1.2053 0.2628 0.084 Uiso 1 1 calc R . .
H4MC H 1.3964 1.1784 0.1924 0.084 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 117.2(3) . . ?
C6 C1 C28 120.2(3) . . ?
C2 C1 C28 122.6(3) . . ?
C3 C2 C1 123.4(3) . . ?
C3 C2 H2 118.3 . . ?
C1 C2 H2 118.3 . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 C7 119.8(3) . . ?
C2 C3 C7 123.1(3) . . ?
O4 C4 C5 121.2(3) . . ?
O4 C4 C3 117.3(3) . . ?
C5 C4 C3 121.5(3) . . ?
C4 O4 H4 110(3) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
O6 C6 C5 120.7(3) . . ?
O6 C6 C1 117.8(3) . . ?
C5 C6 C1 121.4(3) . . ?
C6 O6 H6 107(3) . . ?
C29 C7 C3 113.6(2) . . ?
C29 C7 C8 112.3(2) . . ?
C3 C7 C8 110.4(2) . . ?
C29 C7 H7 106.7 . . ?
C3 C7 H7 106.7 . . ?
C8 C7 H7 106.7 . . ?
C9 C8 C13 117.0(3) . . ?
C9 C8 C7 119.4(3) . . ?
C13 C8 C7 123.5(3) . . ?
C10 C9 C8 123.8(3) . . ?
C10 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C11 C10 C9 117.2(3) . . ?
C11 C10 C14 122.3(3) . . ?
C9 C10 C14 120.5(3) . . ?
O11 C11 C12 120.7(3) . . ?
O11 C11 C10 118.2(3) . . ?
C12 C11 C10 121.1(3) . . ?
C11 O11 H11 111(3) . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
O13 C13 C12 115.9(3) . . ?
O13 C13 C8 123.3(3) . . ?
C12 C13 C8 120.7(3) . . ?
C13 O13 H13 110(3) . . ?
C15 C14 C10 111.1(2) . . ?
C15 C14 C32 113.5(3) . . ?
C10 C14 C32 111.1(2) . . ?
C15 C14 H14 106.9 . . ?
C10 C14 H14 106.9 . . ?
C32 C14 H14 106.9 . . ?
C16 C15 C20 116.8(3) . . ?
C16 C15 C14 122.7(3) . . ?
C20 C15 C14 120.4(3) . . ?
C16 C17 C18 116.7(3) . . ?
C16 C17 C21 123.0(3) . . ?
C18 C17 C21 120.3(3) . . ?
C15 C16 C17 124.5(3) . . ?
C15 C16 H16 117.8 . . ?
C17 C16 H16 117.8 . . ?
O18 C18 C19 115.4(3) . . ?
O18 C18 C17 123.8(3) . . ?
C19 C18 C17 120.8(3) . . ?
C18 O18 H18 111(3) . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
O20 C20 C19 115.7(3) . . ?
O20 C20 C15 123.2(3) . . ?
C19 C20 C15 121.0(3) . . ?
C20 O20 H20 111(3) . . ?
C17 C21 C22 110.1(2) . . ?
C17 C21 C35 114.1(2) . . ?
C22 C21 C35 111.5(2) . . ?
C17 C21 H21 106.9 . . ?
C22 C21 H21 106.9 . . ?
C35 C21 H21 106.9 . . ?
C23 C22 C27 116.3(3) . . ?
C23 C22 C21 121.3(3) . . ?
C27 C22 C21 122.4(3) . . ?
C22 C23 C24 124.7(3) . . ?
C22 C23 H23 117.7 . . ?
C24 C23 H23 117.7 . . ?
C23 C24 C25 116.4(3) . . ?
C23 C24 C28 120.1(3) . . ?
C25 C24 C28 123.4(3) . . ?
O25 C25 C26 115.6(3) . . ?
O25 C25 C24 123.5(3) . . ?
C26 C25 C24 120.9(3) . . ?
C25 O25 H25 108(3) . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
O27 C27 C26 122.0(3) . . ?
O27 C27 C22 117.0(3) . . ?
C26 C27 C22 121.0(3) . . ?
C27 O27 H27 110(3) . . ?
C1 C28 C24 111.7(3) . . ?
C1 C28 C38 113.1(3) . . ?
C24 C28 C38 112.0(3) . . ?
C1 C28 H28 106.5 . . ?
C24 C28 H28 106.5 . . ?
C38 C28 H28 106.5 . . ?
C7 C29 C30 113.9(3) . . ?
C7 C29 H29A 108.8 . . ?
C30 C29 H29A 108.8 . . ?
C7 C29 H29B 108.8 . . ?
C30 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C33 C32 C14 113.1(3) . . ?
C33 C32 H32A 109.0 . . ?
C14 C32 H32A 109.0 . . ?
C33 C32 H32B 109.0 . . ?
C14 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C31 C30 C29 112.4(3) . . ?
C31 C30 H30A 109.1 . . ?
C29 C30 H30A 109.1 . . ?
C31 C30 H30B 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C34 C33 C32 112.5(3) . . ?
C34 C33 H33A 109.1 . . ?
C32 C33 H33A 109.1 . . ?
C34 C33 H33B 109.1 . . ?
C32 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C21 113.2(2) . . ?
C36 C35 H35A 108.9 . . ?
C21 C35 H35A 108.9 . . ?
C36 C35 H35B 108.9 . . ?
C21 C35 H35B 108.9 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 113.8(3) . . ?
C37 C36 H36A 108.8 . . ?
C35 C36 H36A 108.8 . . ?
C37 C36 H36B 108.8 . . ?
C35 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 C28 113.7(3) . . ?
C39 C38 H38A 108.8 . . ?
C28 C38 H38A 108.8 . . ?
C39 C38 H38B 108.8 . . ?
C28 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C40 C39 C38 112.6(3) . . ?
C40 C39 H39A 109.1 . . ?
C38 C39 H39A 109.1 . . ?
C40 C39 H39B 109.1 . . ?
C38 C39 H39B 109.1 . . ?
H39A C39 H39B 107.8 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C57 N2 C55 109.1(3) . . ?
C57 N2 C50 110.5(3) . . ?
C55 N2 C50 110.8(3) . . ?
C57 N2 C53 107.7(3) . . ?
C55 N2 C53 109.0(3) . . ?
C50 N2 C53 109.8(3) . . ?
C51 N1 C56 110.8(3) . . ?
C51 N1 C54 110.9(3) . . ?
C56 N1 C54 108.9(3) . . ?
C51 N1 C52 110.1(3) . . ?
C56 N1 C52 108.0(3) . . ?
C54 N1 C52 108.1(3) . . ?
N2 C50 H50A 109.5 . . ?
N2 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
N2 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
N1 C51 H51A 109.5 . . ?
N1 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N1 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N1 C52 C53 109.8(3) . . ?
N1 C52 H52A 109.7 . . ?
C53 C52 H52A 109.7 . . ?
N1 C52 H52B 109.7 . . ?
C53 C52 H52B 109.7 . . ?
H52A C52 H52B 108.2 . . ?
N1 C54 C55 109.0(3) . . ?
N1 C54 H54A 109.9 . . ?
C55 C54 H54A 109.9 . . ?
N1 C54 H54B 109.9 . . ?
C55 C54 H54B 109.9 . . ?
H54A C54 H54B 108.3 . . ?
N2 C55 C54 110.0(3) . . ?
N2 C55 H55A 109.7 . . ?
C54 C55 H55A 109.7 . . ?
N2 C55 H55B 109.7 . . ?
C54 C55 H55B 109.7 . . ?
H55A C55 H55B 108.2 . . ?
N2 C53 C52 108.8(3) . . ?
N2 C53 H53A 109.9 . . ?
C52 C53 H53A 109.9 . . ?
N2 C53 H53B 109.9 . . ?
C52 C53 H53B 109.9 . . ?
H53A C53 H53B 108.3 . . ?
N1 C56 C57 109.1(3) . . ?
N1 C56 H56A 109.9 . . ?
C57 C56 H56A 109.9 . . ?
N1 C56 H56B 109.9 . . ?
C57 C56 H56B 109.9 . . ?
H56A C56 H56B 108.3 . . ?
N2 C57 C56 110.0(3) . . ?
N2 C57 H57A 109.7 . . ?
C56 C57 H57A 109.7 . . ?
N2 C57 H57B 109.7 . . ?
C56 C57 H57B 109.7 . . ?
H57A C57 H57B 108.2 . . ?
C2M O1M H1M 109.5 . . ?
O1M C2M H2MA 109.5 . . ?
O1M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O1M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?
C4M O3M H3M 106(3) . . ?
O3M C4M H4MA 109.5 . . ?
O3M C4M H4MB 109.5 . . ?
H4MA C4M H4MB 109.5 . . ?
O3M C4M H4MC 109.5 . . ?
H4MA C4M H4MC 109.5 . . ?
H4MB C4M H4MC 109.5 . . ?
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 C6 1.392(4) . ?
C1 C2 1.395(4) . ?
C1 C28 1.527(4) . ?
C2 C3 1.393(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(4) . ?
C3 C7 1.529(4) . ?
C4 O4 1.374(4) . ?
C4 C5 1.391(4) . ?
O4 H4 0.831(18) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 O6 1.382(4) . ?
O6 H6 0.843(18) . ?
C7 C29 1.525(4) . ?
C7 C8 1.530(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.396(4) . ?
C8 C13 1.397(4) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(4) . ?
C10 C14 1.532(4) . ?
C11 O11 1.380(4) . ?
C11 C12 1.390(4) . ?
O11 H11 0.826(18) . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 O13 1.374(4) . ?
O13 H13 0.836(18) . ?
C14 C15 1.526(4) . ?
C14 C32 1.534(4) . ?
C14 H14 1.0000 . ?
C15 C16 1.386(4) . ?
C15 C20 1.402(4) . ?
C17 C16 1.393(4) . ?
C17 C18 1.401(4) . ?
C17 C21 1.521(4) . ?
C16 H16 0.9500 . ?
C18 O18 1.369(4) . ?
C18 C19 1.394(5) . ?
O18 H18 0.838(19) . ?
C19 C20 1.384(4) . ?
C19 H19 0.9500 . ?
C20 O20 1.370(4) . ?
O20 H20 0.838(18) . ?
C21 C22 1.531(4) . ?
C21 C35 1.537(4) . ?
C21 H21 1.0000 . ?
C22 C23 1.391(4) . ?
C22 C27 1.397(4) . ?
C23 C24 1.393(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(4) . ?
C24 C28 1.529(4) . ?
C25 O25 1.378(4) . ?
C25 C26 1.386(4) . ?
O25 H25 0.837(19) . ?
C26 C27 1.385(4) . ?
C26 H26 0.9500 . ?
C27 O27 1.382(4) . ?
O27 H27 0.836(18) . ?
C28 C38 1.534(4) . ?
C28 H28 1.0000 . ?
C29 C30 1.527(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C32 C33 1.523(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C30 C31 1.518(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C33 C34 1.517(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.524(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.523(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.520(4) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.517(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
N2 C57 1.480(4) . ?
N2 C55 1.493(5) . ?
N2 C50 1.499(4) . ?
N2 C53 1.502(4) . ?
N1 C51 1.497(4) . ?
N1 C56 1.497(4) . ?
N1 C54 1.503(4) . ?
N1 C52 1.505(4) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C53 1.527(5) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C54 C55 1.518(5) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C56 C57 1.520(5) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
O1M C2M 1.391(6) . ?
O1M H1M 0.8400 . ?
C2M H2MA 0.9800 . ?
C2M H2MB 0.9800 . ?
C2M H2MC 0.9800 . ?
O3M C4M 1.419(5) . ?
O3M H3M 0.837(19) . ?
C4M H4MA 0.9800 . ?
C4M H4MB 0.9800 . ?
C4M H4MC 0.9800 . ?
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
O4 H4 Cl1 0.831(18) 2.25(2) 3.064(2) 165(4) .
O6 H6 Cl1 0.843(18) 2.30(2) 3.129(2) 169(4) 2_676
O11 H11 Cl2 0.826(18) 2.20(2) 3.006(3) 165(4) .
O13 H13 O4 0.836(18) 1.95(2) 2.755(3) 163(4) .
O25 H25 O6 0.837(19) 2.04(2) 2.847(3) 161(4) .
O27 H27 O3M 0.836(18) 1.837(19) 2.670(3) 173(4) .
O1M H1M Cl2 0.84 2.77 3.283(6) 121.5 .
O18 H18 O27 0.838(19) 1.93(2) 2.751(3) 166(4) .
O20 H20 O11 0.838(18) 1.95(2) 2.767(3) 165(4) .
O3M H3M Cl1 0.837(19) 2.26(2) 3.080(3) 165(4) 2_776
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(4) . . . . ?
C28 C1 C2 C3 178.9(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C7 -178.8(3) . . . . ?
C2 C3 C4 O4 -178.1(3) . . . . ?
C7 C3 C4 O4 0.3(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C7 C3 C4 C5 179.6(3) . . . . ?
O4 C4 C5 C6 178.5(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 O6 179.9(3) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C2 C1 C6 O6 -179.2(3) . . . . ?
C28 C1 C6 O6 1.2(4) . . . . ?
C2 C1 C6 C5 1.2(5) . . . . ?
C28 C1 C6 C5 -178.4(3) . . . . ?
C4 C3 C7 C29 150.0(3) . . . . ?
C2 C3 C7 C29 -31.7(4) . . . . ?
C4 C3 C7 C8 -82.8(3) . . . . ?
C2 C3 C7 C8 95.6(3) . . . . ?
C29 C7 C8 C9 46.9(4) . . . . ?
C3 C7 C8 C9 -81.0(3) . . . . ?
C29 C7 C8 C13 -131.3(3) . . . . ?
C3 C7 C8 C13 100.8(3) . . . . ?
C13 C8 C9 C10 2.6(4) . . . . ?
C7 C8 C9 C10 -175.7(3) . . . . ?
C8 C9 C10 C11 -2.5(4) . . . . ?
C8 C9 C10 C14 175.3(3) . . . . ?
C9 C10 C11 O11 -178.8(3) . . . . ?
C14 C10 C11 O11 3.5(4) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C14 C10 C11 C12 -177.0(3) . . . . ?
O11 C11 C12 C13 -179.8(3) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 O13 178.8(3) . . . . ?
C11 C12 C13 C8 -0.6(4) . . . . ?
C9 C8 C13 O13 179.7(3) . . . . ?
C7 C8 C13 O13 -2.1(5) . . . . ?
C9 C8 C13 C12 -1.0(4) . . . . ?
C7 C8 C13 C12 177.2(3) . . . . ?
C11 C10 C14 C15 -102.4(3) . . . . ?
C9 C10 C14 C15 80.0(3) . . . . ?
C11 C10 C14 C32 130.2(3) . . . . ?
C9 C10 C14 C32 -47.4(4) . . . . ?
C10 C14 C15 C16 -98.5(3) . . . . ?
C32 C14 C15 C16 27.6(4) . . . . ?
C10 C14 C15 C20 80.4(4) . . . . ?
C32 C14 C15 C20 -153.5(3) . . . . ?
C20 C15 C16 C17 -0.1(5) . . . . ?
C14 C15 C16 C17 178.8(3) . . . . ?
C18 C17 C16 C15 0.4(5) . . . . ?
C21 C17 C16 C15 -176.1(3) . . . . ?
C16 C17 C18 O18 180.0(3) . . . . ?
C21 C17 C18 O18 -3.4(5) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C21 C17 C18 C19 176.6(3) . . . . ?
O18 C18 C19 C20 179.4(3) . . . . ?
C17 C18 C19 C20 -0.6(5) . . . . ?
C18 C19 C20 O20 -178.0(3) . . . . ?
C18 C19 C20 C15 0.9(5) . . . . ?
C16 C15 C20 O20 178.3(3) . . . . ?
C14 C15 C20 O20 -0.7(5) . . . . ?
C16 C15 C20 C19 -0.6(5) . . . . ?
C14 C15 C20 C19 -179.5(3) . . . . ?
C16 C17 C21 C22 97.8(3) . . . . ?
C18 C17 C21 C22 -78.6(3) . . . . ?
C16 C17 C21 C35 -28.4(4) . . . . ?
C18 C17 C21 C35 155.2(3) . . . . ?
C17 C21 C22 C23 -79.1(4) . . . . ?
C35 C21 C22 C23 48.5(4) . . . . ?
C17 C21 C22 C27 101.2(3) . . . . ?
C35 C21 C22 C27 -131.1(3) . . . . ?
C27 C22 C23 C24 1.9(5) . . . . ?
C21 C22 C23 C24 -177.8(3) . . . . ?
C22 C23 C24 C25 -4.5(5) . . . . ?
C22 C23 C24 C28 172.0(3) . . . . ?
C23 C24 C25 O25 -177.6(3) . . . . ?
C28 C24 C25 O25 6.0(5) . . . . ?
C23 C24 C25 C26 4.0(5) . . . . ?
C28 C24 C25 C26 -172.4(3) . . . . ?
O25 C25 C26 C27 -179.7(3) . . . . ?
C24 C25 C26 C27 -1.2(5) . . . . ?
C25 C26 C27 O27 179.9(3) . . . . ?
C25 C26 C27 C22 -1.5(5) . . . . ?
C23 C22 C27 O27 179.8(3) . . . . ?
C21 C22 C27 O27 -0.5(4) . . . . ?
C23 C22 C27 C26 1.2(5) . . . . ?
C21 C22 C27 C26 -179.1(3) . . . . ?
C6 C1 C28 C24 86.0(3) . . . . ?
C2 C1 C28 C24 -93.6(3) . . . . ?
C6 C1 C28 C38 -146.6(3) . . . . ?
C2 C1 C28 C38 33.8(4) . . . . ?
C23 C24 C28 C1 81.7(4) . . . . ?
C25 C24 C28 C1 -102.1(3) . . . . ?
C23 C24 C28 C38 -46.3(4) . . . . ?
C25 C24 C28 C38 130.0(3) . . . . ?
C3 C7 C29 C30 -174.3(3) . . . . ?
C8 C7 C29 C30 59.4(3) . . . . ?
C15 C14 C32 C33 173.4(3) . . . . ?
C10 C14 C32 C33 -60.5(3) . . . . ?
C7 C29 C30 C31 -177.2(3) . . . . ?
C14 C32 C33 C34 -176.2(3) . . . . ?
C17 C21 C35 C36 -172.2(3) . . . . ?
C22 C21 C35 C36 62.3(3) . . . . ?
C21 C35 C36 C37 -178.4(3) . . . . ?
C1 C28 C38 C39 176.9(3) . . . . ?
C24 C28 C38 C39 -55.8(4) . . . . ?
C28 C38 C39 C40 -177.7(3) . . . . ?
C51 N1 C52 C53 171.3(3) . . . . ?
C56 N1 C52 C53 -67.7(4) . . . . ?
C54 N1 C52 C53 50.1(4) . . . . ?
C51 N1 C54 C55 170.6(3) . . . . ?
C56 N1 C54 C55 48.4(4) . . . . ?
C52 N1 C54 C55 -68.7(4) . . . . ?
C57 N2 C55 C54 -68.1(4) . . . . ?
C50 N2 C55 C54 170.2(3) . . . . ?
C53 N2 C55 C54 49.2(4) . . . . ?
N1 C54 C55 N2 16.7(4) . . . . ?
C57 N2 C53 C52 50.7(4) . . . . ?
C55 N2 C53 C52 -67.5(4) . . . . ?
C50 N2 C53 C52 171.0(3) . . . . ?
N1 C52 C53 N2 15.2(4) . . . . ?
C51 N1 C56 C57 169.6(3) . . . . ?
C54 N1 C56 C57 -68.1(4) . . . . ?
C52 N1 C56 C57 49.0(4) . . . . ?
C55 N2 C57 C56 48.2(4) . . . . ?
C50 N2 C57 C56 170.2(3) . . . . ?
C53 N2 C57 C56 -69.9(4) . . . . ?
N1 C56 C57 N2 16.9(4) . . . . ?
