#------------------------------------------------------------------------------
#$Date: 2016-12-21 15:04:25 +0200 (Wed, 21 Dec 2016) $
#$Revision: 189303 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/48/1544830.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_1544830
loop_
_publ_author_name
'Roszak, Kinga'
'Katrusiak, Andrzej'
'Dega-Szafran, Zofia'
'Komasa, Anna'
'Kowalczyk, Iwona'
'Szafran, Mirosław'
_publ_contact_author_address
;
Faculty of Chemistry,
Adam Mickiewicz University,
Umultowska 89b, 61-614 Poznań
Poland
;
_publ_contact_author_email       katran@amu.edu.pl
_publ_contact_author_fax         +48(61)8291555
_publ_contact_author_name
;
Andrzej Katrusiak
;
_publ_contact_author_phone       +48(61)8291590
_publ_section_title
;
 Conformational flexibility and pseudosymmetric aggregation in a betainium
 salt hydrate
;
_journal_name_full               'Structural Chemistry'
_journal_paper_doi               10.1007/s11224-016-0889-4
_journal_year                    2016
_chemical_formula_moiety         'C10 H14 N O2, I, H2 O'
_chemical_formula_sum            'C10 H16 I N O3'
_chemical_formula_weight         325.14
_chemical_name_common
;
3-(trimethylammonium)-benzoic acid iodide hydrate
;
_chemical_name_systematic
;
3-(trimethylammonium)-benzoic acid iodide hydrate
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 118.610(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.5130(11)
_cell_length_b                   7.6986(4)
_cell_length_c                   19.5890(10)
_cell_measurement_reflns_used    11200
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.29
_cell_measurement_theta_min      2.90
_cell_volume                     2583.4(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics
;X-Seed (Barbour, 2001) 
and POV-Ray (Persistence of Vision, 2004)
Mercury (2008)
;
_computing_publication_material  'SHELXL (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      210(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23038
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (2014).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.186
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         11200
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0535
_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)+(0.0118P)²+0.3622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                10895
_reflns_number_total             11200
_reflns_threshold_expression     >2sigma(I)
_journal_article_reference       'Structural Chemistry'
_cod_data_source_file            CIF.cif
_cod_data_source_block           210K
_cod_original_cell_volume        2583.4(2)
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               1544830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
I1 I 0.1335(2) 0.9738(4) 0.1800(2) 0.0426(1) Uani 1 1 d DU . .
I2 I -0.1872(2) 0.4854(4) 0.0110(2) 0.0463(1) Uani 1 1 d DU . .
I3 I 0.3016(2) 0.5256(4) -0.0014(2) 0.0426(1) Uani 1 1 d DU . .
I4 I 0.6227(2) 0.9844(4) 0.6679(2) 0.0459(1) Uani 1 1 d DU . .
O1 O -0.12280(4) 0.87000(3) -0.13930(3) 0.05200(8) Uani 1 1 d U . .
H1 H -0.1605 0.8141 -0.1438 0.078 Uiso 1 1 calc RD . .
O2 O -0.14990(2) 1.0470(3) -0.0638(1) 0.0440(6) Uani 1 1 d U . .
C7 C -0.11000(9) 1.0020(4) -0.0910(2) 0.0340(2) Uani 1 1 d U . .
C1 C -0.03500(2) 1.0930(6) -0.0720(2) 0.0280(1) Uani 1 1 d DU . .
C2 C -0.01750(8) 1.2490(4) -0.0268(6) 0.0180(8) Uani 1 1 d U . .
H2 H -0.0506 1.2950 -0.0096 0.022 Uiso 1 1 calc R . .
C3 C 0.06060(8) 1.33500(5) -0.00860(8) 0.03200(9) Uani 1 1 d U . .
C4 C 0.10300(3) 1.27500(5) -0.03800(2) 0.03900(3) Uani 1 1 d DU . .
H4 H 0.1495 1.3323 -0.0261 0.046 Uiso 1 1 calc R . .
C5 C 0.08390(6) 1.13700(4) -0.08310(7) 0.02500(8) Uani 1 1 d DU . .
H5 H 0.1160 1.1034 -0.1038 0.030 Uiso 1 1 calc RD . .
C6 C 0.02090(7) 1.04600(5) -0.10000(2) 0.03700(1) Uani 1 1 d DU . .
H6 H 0.0110 0.9480 -0.1309 0.045 Uiso 1 1 calc R . .
N1 N 0.07300(2) 1.49800(4) 0.037900(7) 0.03000(9) Uani 1 1 d U . .
C8 C 0.026900(2) 1.5180(3) 0.07760(2) 0.04500(6) Uani 1 1 d U . .
H8A H -0.0257 1.5488 0.0406 0.068 Uiso 1 1 calc R . .
H8B H 0.0491 1.6087 0.1159 0.068 Uiso 1 1 calc R . .
H8C H 0.0270 1.4113 0.1027 0.068 Uiso 1 1 calc R . .
C9 C 0.16020(1) 1.4630(2) 0.11130(9) 0.02400(4) Uani 1 1 d U . .
H9A H 0.1594 1.3594 0.1380 0.036 Uiso 1 1 calc R . .
H9B H 0.1753 1.5599 0.1465 0.036 Uiso 1 1 calc R . .
H9C H 0.1971 1.4499 0.0923 0.036 Uiso 1 1 calc R . .
C10 C 0.07790(2) 1.64300(3) -0.00200(1) 0.03400(5) Uani 1 1 d U . .
H10A H 0.1190 1.6259 -0.0150 0.051 Uiso 1 1 calc R . .
H10B H 0.0890 1.7440 0.0303 0.051 Uiso 1 1 calc R . .
H10C H 0.0293 1.6587 -0.0487 0.051 Uiso 1 1 calc R . .
O11 O 0.06930(2) 1.53800(3) 0.26280(3) 0.0420(6) Uani 1 1 d U . .
H11 H 0.1074 1.4743 0.2770 0.063 Uiso 1 1 calc RD . .
O12 O 0.02340(4) 1.3340(3) 0.31180(3) 0.04800(7) Uani 1 1 d U . .
C17 C 0.02200(2) 1.47400(5) 0.28600(2) 0.04800(3) Uani 1 1 d U . .
C11 C -0.05130(9) 1.59000(5) 0.26520(8) 0.02600(9) Uani 1 1 d DU . .
C12 C -0.05900(2) 1.74100(5) 0.21800(2) 0.02700(1) Uani 1 1 d U . .
H12 H -0.0213 1.7686 0.2029 0.032 Uiso 1 1 calc R . .
C13 C -0.12400(3) 1.8390(6) 0.19700(2) 0.03800(2) Uani 1 1 d U . .
C14 C -0.17900(2) 1.8030(6) 0.22000(2) 0.03300(1) Uani 1 1 d U . .
H14 H -0.2217 1.8755 0.2068 0.040 Uiso 1 1 calc R . .
C15 C -0.16800(3) 1.6500(7) 0.26500(2) 0.0460(3) Uani 1 1 d U . .
H15 H -0.2045 1.6223 0.2811 0.056 Uiso 1 1 calc R . .
C16 C -0.10860(8) 1.5480(5) 0.28430(9) 0.03000(9) Uani 1 1 d DU . .
H16 H -0.1047 1.4459 0.3113 0.036 Uiso 1 1 calc R . .
N2 N -0.1420(2) 1.9980(4) 0.1440(2) 0.0290(1) Uani 1 1 d DU . .
C18 C -0.0746(7) 2.0510(4) 0.13420(7) 0.06500(1) Uani 1 1 d DU . .
H18A H -0.0292 2.0623 0.1842 0.097 Uiso 1 1 calc R . .
H18B H -0.0856 2.1597 0.1072 0.097 Uiso 1 1 calc R . .
H18C H -0.0652 1.9638 0.1045 0.097 Uiso 1 1 calc R . .
C19 C -0.22100(2) 1.98000(5) 0.07400(2) 0.06200(2) Uani 1 1 d U . .
H19A H -0.2216 1.8781 0.0457 0.093 Uiso 1 1 calc R . .
H19B H -0.2318 2.0804 0.0421 0.093 Uiso 1 1 calc R . .
H19C H -0.2601 1.9685 0.0906 0.093 Uiso 1 1 calc R . .
C20 C -0.15300(3) 2.15500(6) 0.18600(3) 0.06200(5) Uani 1 1 d U . .
H20A H -0.1976 2.1383 0.1930 0.093 Uiso 1 1 calc R . .
H20B H -0.1596 2.2573 0.1553 0.093 Uiso 1 1 calc R . .
H20C H -0.1071 2.1682 0.2358 0.093 Uiso 1 1 calc R . .
O21 O 0.550900(3) 1.64300(3) 0.30770(2) 0.03400(6) Uani 1 1 d DU . .
H21 H 0.5968 1.6725 0.3271 0.051 Uiso 1 1 calc RD . .
O22 O 0.59450(2) 1.4310(3) 0.26000(1) 0.04400(6) Uani 1 1 d DU . .
C27 C 0.54140(6) 1.4890(4) 0.2720(2) 0.03100(1) Uani 1 1 d DU . .
C21 C 0.46700(2) 1.3990(6) 0.2540(2) 0.02900(1) Uani 1 1 d U . .
C22 C 0.44700(2) 1.2620(5) 0.20780(9) 0.03500(1) Uani 1 1 d U . .
H22 H 0.4813 1.2284 0.1892 0.042 Uiso 1 1 calc R . .
C23 C 0.38600(6) 1.1730(4) 0.1872(5) 0.0150(7) Uani 1 1 d U . .
C24 C 0.33300(3) 1.2240(5) 0.2160(2) 0.0370(2) Uani 1 1 d U . .
H24 H 0.2893 1.1581 0.2059 0.044 Uiso 1 1 calc R . .
C25 C 0.3510(2) 1.3860(5) 0.2600(2) 0.0430(1) Uani 1 1 d DU . .
H25 H 0.3167 1.4311 0.2760 0.051 Uiso 1 1 calc RD . .
C26 C 0.42280(7) 1.4720(4) 0.27930(8) 0.02300(7) Uani 1 1 d DU . .
H26 H 0.4374 1.5739 0.3081 0.027 Uiso 1 1 calc R . .
N3 N 0.3560(2) 1.0170(4) 0.13380(8) 0.03200(9) Uani 1 1 d U . .
C28 C 0.3784(5) 1.0330(3) 0.07100(3) 0.06500(8) Uani 1 1 d U . .
H28A H 0.3595 1.1417 0.0444 0.097 Uiso 1 1 calc R . .
H28B H 0.3557 0.9392 0.0348 0.097 Uiso 1 1 calc R . .
H28C H 0.4342 1.0290 0.0933 0.097 Uiso 1 1 calc R . .
C29 C 0.27830(8) 0.96000(4) 0.10150(7) 0.0650(2) Uani 1 1 d U . .
H29A H 0.2689 0.9156 0.1420 0.097 Uiso 1 1 calc R . .
H29B H 0.2692 0.8699 0.0642 0.097 Uiso 1 1 calc R . .
H29C H 0.2438 1.0556 0.0762 0.097 Uiso 1 1 calc R . .
C30 C 0.41460(6) 0.86100(4) 0.18570(4) 0.06500(9) Uani 1 1 d U . .
H30A H 0.4642 0.9084 0.2222 0.097 Uiso 1 1 calc R . .
H30B H 0.4217 0.7803 0.1521 0.097 Uiso 1 1 calc R . .
H30C H 0.3921 0.8010 0.2132 0.097 Uiso 1 1 calc R . .
O31 O 0.35820(1) 1.0550(3) 0.40450(2) 0.0440(7) Uani 1 1 d DU . .
H31 H 0.3242 0.9816 0.3943 0.067 Uiso 1 1 calc RD . .
O32 O 0.40100(4) 0.8500(3) 0.35510(3) 0.0490(7) Uani 1 1 d DU . .
C37 C 0.41620(4) 0.9860(4) 0.39400(8) 0.0250(1) Uani 1 1 d DU . .
C31 C 0.48100(2) 1.0980(5) 0.41930(8) 0.0280(9) Uani 1 1 d DU . .
C32 C 0.49500(2) 1.2450(5) 0.46300(2) 0.0290(1) Uani 1 1 d U . .
H32 H 0.4592 1.2816 0.4780 0.035 Uiso 1 1 calc R . .
C33 C 0.56200(2) 1.3400(5) 0.48440(9) 0.0200(9) Uani 1 1 d U . .
C34 C 0.61500(2) 1.2940(6) 0.46200(2) 0.0370(2) Uani 1 1 d U . .
H34 H 0.6606 1.3582 0.4783 0.044 Uiso 1 1 calc R . .
C35 C 0.60200(2) 1.15000(5) 0.41420(9) 0.02700(1) Uani 1 1 d DU . .
H35 H 0.6381 1.1189 0.3977 0.033 Uiso 1 1 calc R . .
C36 C 0.53210(8) 1.05100(5) 0.39120(8) 0.0300(9) Uani 1 1 d DU . .
H36 H 0.52070 0.95720 0.35780 0.03600 Uiso 1 1 calc R . .
N4 N 0.5770(2) 1.5020(4) 0.5340(2) 0.0290(1) Uani 1 1 d DU . .
C38 C 0.51930(3) 1.5220(3) 0.56400(3) 0.02800(6) Uani 1 1 d U . .
H38A H 0.4684 1.5460 0.5215 0.043 Uiso 1 1 calc R . .
H38B H 0.5352 1.6159 0.6007 0.043 Uiso 1 1 calc R . .
H38C H 0.5175 1.4163 0.5892 0.043 Uiso 1 1 calc R . .
C39 C 0.58470(6) 1.65900(3) 0.49480(6) 0.01900(7) Uani 1 1 d DU . .
H39A H 0.6240 1.6411 0.4794 0.029 Uiso 1 1 calc R . .
H39B H 0.5992 1.7558 0.5301 0.029 Uiso 1 1 calc R . .
H39C H 0.5356 1.6834 0.4497 0.029 Uiso 1 1 calc R . .
C40 C 0.64930(7) 1.4740(4) 0.61140(6) 0.02900(7) Uani 1 1 d U . .
H40A H 0.6439 1.3674 0.6340 0.043 Uiso 1 1 calc R . .
H40B H 0.6550 1.5689 0.6455 0.043 Uiso 1 1 calc R . .
H40C H 0.6945 1.4673 0.6042 0.043 Uiso 1 1 calc R . .
O4W O 0.2384(1) 0.8490(2) 0.3751(7) 0.030(5) Uani 1 1 d GU . .
H14W H 0.2433 0.7585 0.4024 0.045 Uiso 1 1 d GD . .
H24W H 0.1910 0.8582 0.3395 0.045 Uiso 1 1 d GD . .
O1W O -0.2421(11) 0.679(3) -0.1710(11) 0.045(7) Uani 1 1 d GU . .
H11W H -0.2471 0.5771 -0.1569 0.068 Uiso 1 1 d GD . .
H21W H -0.2867 0.7175 -0.2043 0.068 Uiso 1 1 d GD . .
O3W O 0.6840(15) 1.812(4) 0.3539(13) 0.030(1) Uani 1 1 d GU . .
H13W H 0.7221 1.7543 0.3882 0.045 Uiso 1 1 d GD . .
H23W H 0.6823 1.7991 0.3098 0.045 Uiso 1 1 d GD . .
O2W O 0.1906(16) 1.348(4) 0.2994(12) 0.030(1) Uani 1 1 d GU . .
H12W H 0.2354 1.3750 0.3364 0.045 Uiso 1 1 d GD . .
H22W H 0.1851 1.2378 0.2981 0.045 Uiso 1 1 d GD . .
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'
I I -0.4742 1.8119 '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
C7 O1 H1 109.5 . .
O2 C7 O1 127.1(3) . .
O2 C7 C1 121.6(3) . .
O1 C7 C1 111.3(2) . .
C7 C1 C6 127.0(3) . .
C7 C1 C2 117.4(3) . .
C6 C1 C2 115.7(3) . .
C1 C2 C3 115.0(3) . .
C1 C2 H2 122.6 . .
C3 C2 H2 122.6 . .
C4 C3 C2 121.0(3) . .
C4 C3 N1 128.0(3) . .
C2 C3 N1 110.8(3) . .
C5 C4 C3 123.30(9) . .
C5 C4 H4 118.4 . .
C3 C4 H4 118.5 . .
C6 C5 C4 122(4) . .
C6 C5 H5 118.9 . .
C4 C5 H5 119.1 . .
C5 C6 C1 123(3) . .
C5 C6 H6 118.5 . .
C1 C6 H6 118.4 . .
C10 N1 C8 116.26(9) . .
C10 N1 C3 111.36(5) . .
C8 N1 C3 116.92(10) . .
C10 N1 C9 107.61(5) . .
C8 N1 C9 101.34(5) . .
C3 N1 C9 101.11(8) . .
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 H9A 109.5 . .
N1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N1 C10 H10A 109.5 . .
N1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C17 O11 H11 109.6 . .
O12 C17 O11 128.04(6) . .
O12 C17 C11 117.47(7) . .
O11 C17 C11 113.85(6) . .
C16 C11 C12 121.0(3) . .
C16 C11 C17 123.71(15) . .
C12 C11 C17 115.26(12) . .
C13 C12 C11 115.81(15) . .
C13 C12 H12 122.3 . .
C11 C12 H12 122.3 . .
C12 C13 C14 123.4(3) . .
C12 C13 N2 121.75(19) . .
C14 C13 N2 114.9(3) . .
C15 C14 C13 117.3(3) . .
C15 C14 H14 121.3 . .
C13 C14 H14 121.3 . .
C16 C15 C14 122(4) . .
C16 C15 H15 119.1 . .
C14 C15 H15 119.0 . .
C15 C16 C11 120.5(3) . .
C15 C16 H16 119.7 . .
C11 C16 H16 119.7 . .
C19 N2 C20 102.5(2) . .
C19 N2 C13 110.3(2) . .
C20 N2 C13 108.2(2) . .
C19 N2 C18 119.8(3) . .
C20 N2 C18 102.4(3) . .
C13 N2 C18 112.0(3) . .
N2 C18 H18A 109.5 . .
N2 C18 H18B 109.4 . .
H18A C18 H18B 109.5 . .
N2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N2 C19 H19A 109.5 . .
N2 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
N2 C19 H19C 109.4 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N2 C20 H20A 109.3 . .
N2 C20 H20B 109.6 . .
H20A C20 H20B 109.5 . .
N2 C20 H20C 109.6 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C27 O21 H21 109.3 . .
O22 C27 O21 119.5(2) . .
O22 C27 C21 126.2(3) . .
O21 C27 C21 114.0(2) . .
C22 C21 C26 124.7(2) . .
C22 C21 C27 117.9(2) . .
C26 C21 C27 117.0(3) . .
C21 C22 C23 125.3(3) . .
C21 C22 H22 117.8 . .
C23 C22 H22 117.9 . .
C22 C23 C24 118.0(3) . .
C22 C23 N3 130.0(3) . .
C24 C23 N3 112.0(3) . .
C23 C24 C25 116.5(3) . .
C23 C24 H24 121.6 . .
C25 C24 H24 121.7 . .
C24 C25 C26 119.0(3) . .
C24 C25 H25 120.7 . .
C26 C25 H25 120.8 . .
C21 C26 C25 116(3) . .
C21 C26 H26 122.0 . .
C25 C26 H26 121.8 . .
C29 N3 C23 122.4(3) . .
C29 N3 C28 109.5(3) . .
C23 N3 C28 109.5(3) . .
C29 N3 C30 109.5(2) . .
C23 N3 C30 103.3(3) . .
C28 N3 C30 100.3(3) . .
N3 C28 H28A 109.5 . .
N3 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
N3 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
N3 C29 H29A 109.4 . .
N3 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
N3 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
N3 C30 H30A 109.5 . .
N3 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
N3 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C37 O31 H31 109.3 . .
O32 C37 O31 117.0(3) . .
O32 C37 C31 129.83(15) . .
O31 C37 C31 112.4(2) . .
C32 C31 C36 119.68(17) . .
C32 C31 C37 127.14(13) . .
C36 C31 C37 113.0(3) . .
C31 C32 C33 120.47(15) . .
C31 C32 H32 119.7 . .
C33 C32 H32 119.6 . .
C34 C33 C32 121.7(3) . .
C34 C33 N4 119.0(4) . .
C32 C33 N4 119.6(2) . .
C33 C34 C35 120.4(2) . .
C33 C34 H34 119.7 . .
C35 C34 H34 119.7 . .
C34 C35 C36 118.27(9) . .
C34 C35 H35 121.0 . .
C36 C35 H35 121.0 . .
C35 C36 C31 119.30(14) . .
C35 C36 H36 120.3 . .
C31 C36 H36 120.2 . .
C38 N4 C39 113.6(2) . .
C38 N4 C33 112.5(3) . .
C39 N4 C33 112.0(2) . .
C38 N4 C40 97.8(2) . .
C39 N4 C40 111(3) . .
C33 N4 C40 109(3) . .
N4 C38 H38A 109.5 . .
N4 C38 H38B 109.5 . .
H38A C38 H38B 109.5 . .
N4 C38 H38C 109.4 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
N4 C39 H39A 109.6 . .
N4 C39 H39B 109.4 . .
H39A C39 H39B 109.5 . .
N4 C39 H39C 109.4 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
N4 C40 H40A 109.5 . .
N4 C40 H40B 109.5 . .
H40A C40 H40B 109.5 . .
N4 C40 H40C 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
H14W O4W H24W 109.5 . .
H11W O1W H21W 109.5 . .
H13W O3W H23W 109.5 . .
H12W O2W H22W 109.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.328(3) .
O1 H1 0.8200 .
O2 C7 1.186(3) .
C7 C1 1.500(5) .
C1 C6 1.480(4) .
C1 C2 1.440(5) .
C2 C3 1.539(6) .
C2 H2 0.9300 .
C3 C4 1.300(4) .
C3 N1 1.5006(9) .
C4 C5 1.3164(8) .
C4 H4 0.9300 .
C5 C6 1.312(15) .
C5 H5 0.9300 .
C6 H6 0.9300 .
N1 C10 1.3920(4) .
N1 C8 1.4518(5) .
N1 C9 1.6408(14) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
O11 C17 1.3049(6) .
O11 H11 0.8200 .
O12 C17 1.185(2) .
C17 C11 1.5656(16) .
C11 C16 1.380(4) .
C11 C12 1.4477(10) .
C12 C13 1.359(3) .
C12 H12 0.9300 .
C13 C14 1.3765(15) .
C13 N2 1.530(5) .
C14 C15 1.420(5) .
C14 H14 0.9300 .
C15 C16 1.300(5) .
C15 H15 0.9300 .
C16 H16 0.9300 .
N2 C19 1.500(5) .
N2 C20 1.534(3) .
N2 C18 1.475(14) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
O21 C27 1.347(8) .
O21 H21 0.8200 .
O22 C27 1.248(8) .
C27 C21 1.491(4) .
C21 C22 1.320(5) .
C21 C26 1.310(3) .
C22 C23 1.261(5) .
C22 H22 0.9300 .
C23 C24 1.450(4) .
C23 N3 1.510(4) .
C24 C25 1.460(4) .
C24 H24 0.9300 .
C25 C26 1.430(3) .
C25 H25 0.9300 .
C26 H26 0.9300 .
N3 C29 1.405(4) .
N3 C28 1.490(4) .
N3 C30 1.634(3) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
O31 C37 1.3521(18) .
O31 H31 0.8200 .
O32 C37 1.244(3) .
C37 C31 1.410(4) .
C31 C32 1.360(5) .
C31 C36 1.398(2) .
C32 C33 1.377(3) .
C32 H32 0.9300 .
C33 C34 1.3499(19) .
C33 N4 1.520(5) .
C34 C35 1.390(5) .
C34 H34 0.9300 .
C35 C36 1.4338(17) .
C35 H35 0.9300 .
C36 H36 0.9300 .
N4 C38 1.507(4) .
N4 C39 1.478(3) .
N4 C40 1.512(4) .
C38 H38A 0.9600 .
C38 H38B 0.9600 .
C38 H38C 0.9600 .
C39 H39A 0.9600 .
C39 H39B 0.9600 .
C39 H39C 0.9600 .
C40 H40A 0.9600 .
C40 H40B 0.9600 .
C40 H40C 0.9600 .
O4W H14W 0.8528 .
O4W H24W 0.8536 .
O1W H11W 0.8528 .
O1W H21W 0.8524 .
O3W H13W 0.8524 .
O3W H23W 0.8534 .
O2W H12W 0.8524 .
O2W H22W 0.8533 .
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
O2 C7 C1 C6 177.9(3) . . . .
O1 C7 C1 C6 -1.3(5) . . . .
O2 C7 C1 C2 -7.0(6) . . . .
O1 C7 C1 C2 173.8(5) . . . .
C7 C1 C2 C3 179.4(4) . . . .
C6 C1 C2 C3 -5.0(8) . . . .
C1 C2 C3 C4 5.1(8) . . . .
C1 C2 C3 N1 179.3(4) . . . .
C2 C3 C4 C5 -1.6(4) . . . .
N1 C3 C4 C5 -174.64(9) . . . .
C3 C4 C5 C6 -2.03(13) . . . .
C4 C5 C6 C1 1.8(2) . . . .
C7 C1 C6 C5 177.1(3) . . . .
C2 C1 C6 C5 2.0(5) . . . .
C4 C3 N1 C10 55.36(13) . . . .
C2 C3 N1 C10 -118.3(4) . . . .
C4 C3 N1 C8 -167.63(10) . . . .
C2 C3 N1 C8 18.7(4) . . . .
C4 C3 N1 C9 -58.71(12) . . . .
C2 C3 N1 C9 127.7(4) . . . .
O12 C17 C11 C16 8.67(18) . . . .
O11 C17 C11 C16 -179.74(14) . . . .
O12 C17 C11 C12 -166.40(8) . . . .
O11 C17 C11 C12 5.18(10) . . . .
C16 C11 C12 C13 2.3(2) . . . .
C17 C11 C12 C13 177.52(13) . . . .
C11 C12 C13 C14 1.7(3) . . . .
C11 C12 C13 N2 -177.2(2) . . . .
C12 C13 C14 C15 -3.1(4) . . . .
N2 C13 C14 C15 175.9(2) . . . .
C13 C14 C15 C16 0.4(4) . . . .
C14 C15 C16 C11 3.6(4) . . . .
C12 C11 C16 C15 -5.0(3) . . . .
C17 C11 C16 C15 -179.78(19) . . . .
C12 C13 N2 C19 123.8(3) . . . .
C14 C13 N2 C19 -55.1(3) . . . .
C12 C13 N2 C20 -124.8(3) . . . .
C14 C13 N2 C20 56.2(3) . . . .
C12 C13 N2 C18 -12.6(4) . . . .
C14 C13 N2 C18 168.5(2) . . . .
O22 C27 C21 C22 -14.3(5) . . . .
O21 C27 C21 C22 169.0(3) . . . .
O22 C27 C21 C26 172.1(3) . . . .
O21 C27 C21 C26 -4.7(4) . . . .
C26 C21 C22 C23 -6.7(7) . . . .
C27 C21 C22 C23 -179.8(5) . . . .
C21 C22 C23 C24 0.1(8) . . . .
C21 C22 C23 N3 178.6(5) . . . .
C22 C23 C24 C25 6.3(8) . . . .
N3 C23 C24 C25 -172.4(4) . . . .
C23 C24 C25 C26 -7.0(6) . . . .
C22 C21 C26 C25 5.5(5) . . . .
C27 C21 C26 C25 178.6(3) . . . .
C24 C25 C26 C21 1.4(4) . . . .
C22 C23 N3 C29 -163.5(5) . . . .
C24 C23 N3 C29 15.1(6) . . . .
C22 C23 N3 C28 -33.4(8) . . . .
C24 C23 N3 C28 145.2(5) . . . .
C22 C23 N3 C30 72.8(7) . . . .
C24 C23 N3 C30 -108.6(4) . . . .
O32 C37 C31 C32 -179.0(2) . . . .
O31 C37 C31 C32 12.1(3) . . . .
O32 C37 C31 C36 4.5(3) . . . .
O31 C37 C31 C36 -164.37(16) . . . .
C36 C31 C32 C33 -4.9(3) . . . .
C37 C31 C32 C33 178.9(2) . . . .
C31 C32 C33 C34 1.3(4) . . . .
C31 C32 C33 N4 -179.2(2) . . . .
C32 C33 C34 C35 1.8(4) . . . .
N4 C33 C34 C35 -177.7(2) . . . .
C33 C34 C35 C36 -1.3(3) . . . .
C34 C35 C36 C31 -2.2(2) . . . .
C32 C31 C36 C35 5.2(3) . . . .
C37 C31 C36 C35 -178.02(15) . . . .
C34 C33 N4 C38 -171.6(2) . . . .
C32 C33 N4 C38 8.9(4) . . . .
C34 C33 N4 C39 59.0(4) . . . .
C32 C33 N4 C39 -120.5(3) . . . .
C34 C33 N4 C40 -64.3(3) . . . .
C32 C33 N4 C40 116.2(3) . . . .
