#------------------------------------------------------------------------------
#$Date: 2016-12-21 15:04:25 +0200 (Wed, 21 Dec 2016) $
#$Revision: 189303 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/48/1544832.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_1544832
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                 118.580(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.5270(13)
_cell_length_b                   7.7049(3)
_cell_length_c                   19.6170(12)
_cell_measurement_reflns_used    11246
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      29.33
_cell_measurement_theta_min      2.90
_cell_volume                     2591.8(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      230(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  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23094
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.33
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    2.461
_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    1.666
_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         1.142
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.206
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(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   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         11246
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0567
_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)+(0.0218P)²+0.2733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                10852
_reflns_number_total             11246
_reflns_threshold_expression     >2sigma(I)
_journal_article_reference       'Structural Chemistry'
_cod_data_source_file            CIF.cif
_cod_data_source_block           230K
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               1544832
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 0.13330(2) 0.97460(5) 0.18020(2) 0.04740(4) Uani 1 1 d DU . .
I2 I -0.18740(2) 0.48510(5) 0.01090(2) 0.05140(5) Uani 1 1 d DU . .
I3 I 0.30170(2) 0.52620(5) -0.00110(2) 0.04760(3) Uani 1 1 d DU . .
I4 I 0.62280(2) 0.98430(5) 0.66820(2) 0.04980(4) Uani 1 1 d DU . .
O1 O -0.12160(8) 0.8550(4) -0.13340(7) 0.0590(9) Uani 1 1 d DU . .
H1 H -0.1598 0.8035 -0.1365 0.089 Uiso 1 1 calc R . .
O2 O -0.15340(4) 1.05400(3) -0.06540(4) 0.0420(6) Uani 1 1 d DU . .
C7 C -0.11030(8) 1.00200(4) -0.09190(9) 0.0290(8) Uani 1 1 d DU . .
C1 C -0.03300(3) 1.09200(7) -0.07300(3) 0.0270(3) Uani 1 1 d DU . .
C2 C -0.01500(2) 1.24700(6) -0.02700(2) 0.0220(2) Uani 1 1 d U . .
H2 H -0.0482 1.2881 -0.0091 0.027 Uiso 1 1 calc R . .
C3 C 0.05700(2) 1.34000(6) -0.01000(2) 0.02400(1) Uani 1 1 d U . .
C4 C 0.10200(3) 1.27800(6) -0.03700(3) 0.03300(4) Uani 1 1 d DU . .
H4 H 0.1482 1.3357 -0.0235 0.040 Uiso 1 1 calc R . .
C5 C 0.08500(2) 1.13500(6) -0.08300(3) 0.04200(5) Uani 1 1 d DU . .
H5 H 0.1178 1.1011 -0.1025 0.050 Uiso 1 1 calc RD . .
C6 C 0.02200(2) 1.04400(6) -0.09900(3) 0.04100(3) Uani 1 1 d DU . .
H6 H 0.0117 0.9444 -0.1295 0.049 Uiso 1 1 calc R . .
N1 N 0.07400(2) 1.50200(5) 0.03800(2) 0.03500(1) Uani 1 1 d U . .
C8 C 0.026500(5) 1.51900(4) 0.077400(5) 0.04700(8) Uani 1 1 d U . .
H8A H -0.0259 1.5489 0.0401 0.071 Uiso 1 1 calc R . .
H8B H 0.0480 1.6078 0.1162 0.071 Uiso 1 1 calc R . .
H8C H 0.0263 1.4104 0.1016 0.071 Uiso 1 1 calc R . .
C9 C 0.16020(2) 1.46400(3) 0.111500(2) 0.02800(6) Uani 1 1 d U . .
H9A H 0.1585 1.3600 0.1376 0.043 Uiso 1 1 calc R . .
H9B H 0.1755 1.5599 0.1470 0.043 Uiso 1 1 calc R . .
H9C H 0.1973 1.4498 0.0929 0.043 Uiso 1 1 calc R . .
C10 C 0.08060(5) 1.64500(3) -0.00180(3) 0.03800(7) Uani 1 1 d U . .
H10A H 0.1219 1.6253 -0.0143 0.057 Uiso 1 1 calc R . .
H10B H 0.0920 1.7465 0.0301 0.057 Uiso 1 1 calc R . .
H10C H 0.0324 1.6612 -0.0488 0.057 Uiso 1 1 calc R . .
O11 O 0.06890(7) 1.54000(3) 0.263500(7) 0.05000(7) Uani 1 1 d U . .
H11 H 0.1063 1.4735 0.2782 0.075 Uiso 1 1 calc RD . .
O12 O 0.02790(9) 1.35000(4) 0.321300(9) 0.06100(9) Uani 1 1 d U . .
C17 C 0.02200(2) 1.48500(4) 0.28900(2) 0.03300(9) Uani 1 1 d U . .
C11 C -0.04800(3) 1.58800(7) 0.26500(3) 0.03200(3) Uani 1 1 d DU . .
C12 C -0.05800(3) 1.73900(7) 0.21600(3) 0.03800(5) Uani 1 1 d U . .
H12 H -0.0230 1.7664 0.1973 0.046 Uiso 1 1 calc R . .
C13 C -0.12400(3) 1.84100(7) 0.19900(3) 0.03500(3) Uani 1 1 d U . .
C14 C -0.17600(3) 1.79800(8) 0.21900(3) 0.04100(1) Uani 1 1 d U . .
H14 H -0.2195 1.8690 0.2047 0.050 Uiso 1 1 calc R . .
C15 C -0.16900(3) 1.64800(8) 0.26200(3) 0.05000(1) Uani 1 1 d U . .
H15 H -0.2091 1.6143 0.2727 0.060 Uiso 1 1 calc R . .
C16 C -0.10400(3) 1.55500(7) 0.28700(3) 0.03900(1) Uani 1 1 d DU . .
H16 H -0.0963 1.4636 0.3212 0.047 Uiso 1 1 calc R . .
N2 N -0.13900(3) 1.99400(5) 0.14500(2) 0.03400(3) Uani 1 1 d DU . .
C18 C -0.07410(9) 2.05300(5) 0.13350(8) 0.05400(1) Uani 1 1 d DU . .
H18A H -0.0283 2.0647 0.1830 0.080 Uiso 1 1 calc R . .
H18B H -0.0867 2.1625 0.1073 0.080 Uiso 1 1 calc R . .
H18C H -0.0644 1.9691 0.1028 0.080 Uiso 1 1 calc R . .
C19 C -0.22100(3) 1.98000(6) 0.07700(3) 0.05400(7) Uani 1 1 d U . .
H19A H -0.2250 1.8805 0.0465 0.080 Uiso 1 1 calc R . .
H19B H -0.2331 2.0830 0.0459 0.080 Uiso 1 1 calc R . .
H19C H -0.2578 1.9693 0.0968 0.080 Uiso 1 1 calc R . .
C20 C -0.14000(2) 2.15200(6) 0.18400(2) 0.06400(4) Uani 1 1 d U . .
H20A H -0.1840 2.1488 0.1944 0.096 Uiso 1 1 calc R . .
H20B H -0.1452 2.2499 0.1524 0.096 Uiso 1 1 calc R . .
H20C H -0.0929 2.1603 0.2326 0.096 Uiso 1 1 calc R . .
O21 O 0.549400(4) 1.63100(4) 0.313400(3) 0.06100(1) Uani 1 1 d DU . .
H21 H 0.5947 1.6645 0.3337 0.092 Uiso 1 1 calc RD . .
O22 O 0.59550(6) 1.43200(4) 0.259400(7) 0.05600(9) Uani 1 1 d DU . .
C27 C 0.54200(2) 1.48700(5) 0.27100(2) 0.0230(1) Uani 1 1 d DU . .
C21 C 0.46900(3) 1.39800(7) 0.25400(3) 0.0300(3) Uani 1 1 d U . .
C22 C 0.44900(3) 1.26000(7) 0.20800(3) 0.0390(5) Uani 1 1 d U . .
H22 H 0.4833 1.2217 0.1907 0.047 Uiso 1 1 calc R . .
C23 C 0.38400(2) 1.17800(6) 0.18600(2) 0.02600(1) Uani 1 1 d U . .
C24 C 0.33300(3) 1.22800(7) 0.21700(3) 0.04200(6) Uani 1 1 d U . .
H24 H 0.2891 1.1620 0.2078 0.051 Uiso 1 1 calc R . .
C25 C 0.35200(2) 1.38100(6) 0.26100(3) 0.04200(5) Uani 1 1 d DU . .
H25 H 0.3179 1.4239 0.2778 0.050 Uiso 1 1 calc RD . .
C26 C 0.42200(2) 1.46900(5) 0.27900(2) 0.02500(1) Uani 1 1 d DU . .
H26 H 0.4349 1.5724 0.3070 0.030 Uiso 1 1 calc R . .
N3 N 0.35700(2) 1.01700(4) 0.13500(2) 0.0250(1) Uani 1 1 d U . .
C28 C 0.37660(9) 1.03200(4) 0.070700(7) 0.05400(1) Uani 1 1 d U . .
H28A H 0.3576 1.1405 0.0443 0.080 Uiso 1 1 calc R . .
H28B H 0.3527 0.9382 0.0347 0.080 Uiso 1 1 calc R . .
H28C H 0.4322 1.0265 0.0914 0.080 Uiso 1 1 calc R . .
C29 C 0.27900(2) 0.96200(5) 0.10200(2) 0.05004(1) Uani 1 1 d U . .
H29A H 0.2692 0.9179 0.1422 0.080 Uiso 1 1 calc R . .
H29B H 0.2694 0.8729 0.0644 0.080 Uiso 1 1 calc R . .
H29C H 0.2450 1.0589 0.0771 0.080 Uiso 1 1 calc R . .
C30 C 0.415900(8) 0.86200(4) 0.186700(6) 0.05400(9) Uani 1 1 d U . .
H30A H 0.4653 0.9112 0.2231 0.080 Uiso 1 1 calc R . .
H30B H 0.4233 0.7820 0.1534 0.080 Uiso 1 1 calc R . .
H30C H 0.3936 0.8026 0.2144 0.0880 Uiso 1 1 calc R . .
O31 O 0.356300(4) 1.05800(3) 0.40300(6) 0.0520(8) Uani 1 1 d DU . .
H31 H 0.3212 0.9869 0.3933 0.078 Uiso 1 1 calc RD . .
O32 O 0.40480(7) 0.8400(4) 0.36130(8) 0.0520(8) Uani 1 1 d DU . .
C37 C 0.41410(9) 0.9800(4) 0.3960(3) 0.0470(2) Uani 1 1 d DU . .
C31 C 0.48400(3) 1.09800(8) 0.41900(3) 0.0300(4) Uani 1 1 d DU . .
C32 C 0.49500(2) 1.24600(6) 0.46100(2) 0.0210(1) Uani 1 1 d U . .
H32 H 0.4565 1.2837 0.4715 0.025 Uiso 1 1 calc R . .
C33 C 0.56200(3) 1.34000(7) 0.48700(2) 0.0220(1) Uani 1 1 d U . .
C34 C 0.61700(3) 1.29600(7) 0.46100(2) 0.0330(3) Uani 1 1 d U . .
H34 H 0.6622 1.3620 0.4754 0.039 Uiso 1 1 calc R . .
C35 C 0.60100(3) 1.15100(7) 0.41200(2) 0.0350(3) Uani 1 1 d DU . .
H35 H 0.6335 1.1230 0.3918 0.042 Uiso 1 1 calc R . .
C36 C 0.53600(3) 1.04700(7) 0.39500(3) 0.03500(4) Uani 1 1 d DU . .
H36 H 0.5275 0.9443 0.3666 0.042 Uiso 1 1 calc R . .
N4 N 0.5800(3) 1.50100(5) 0.53500(2) 0.0300(2) Uani 1 1 d DU . .
C38 C 0.52270(8) 1.51600(4) 0.568300(7) 0.04300(9) Uani 1 1 d U . .
H38A H 0.4712 1.5400 0.5270 0.065 Uiso 1 1 calc R . .
H38B H 0.5391 1.6085 0.6056 0.065 Uiso 1 1 calc R . .
H38C H 0.5222 1.4089 0.5931 0.065 Uiso 1 1 calc R . .
C39 C 0.59200(9) 1.66300(4) 0.49410(8) 0.03000(8) Uani 1 1 d DU . .
H39A H 0.6318 1.6382 0.4799 0.045 Uiso 1 1 calc R . .
H39B H 0.6078 1.7600 0.5289 0.045 Uiso 1 1 calc R . .
H39C H 0.5441 1.6899 0.4483 0.045 Uiso 1 1 calc R . .
C40 C 0.64940(6) 1.47200(4) 0.61240(6) 0.02000(6) Uani 1 1 d U . .
H40A H 0.6433 1.3659 0.6342 0.030 Uiso 1 1 calc R . .
H40B H 0.6542 1.5672 0.6462 0.030 Uiso 1 1 calc R . .
H40C H 0.6954 1.4661 0.6065 0.030 Uiso 1 1 calc R . .
O4W O 0.23910(3) 0.84500(3) 0.375400(9) 0.0370(7) Uani 1 1 d GU . .
H14W H 0.2444 0.7511 0.4007 0.056 Uiso 1 1 d GD . .
H24W H 0.1920 0.8536 0.3391 0.056 Uiso 1 1 d GD . .
O1W O -0.24120(4) 0.6830(4) -0.17220(4) 0.0640(1) Uani 1 1 d GU . .
H11W H -0.2509 0.5878 -0.1560 0.096 Uiso 1 1 d GD . .
H21W H -0.2839 0.7295 -0.2051 0.096 Uiso 1 1 d GD . .
O3W O 0.68640(4) 1.81500(5) 0.35360(4) 0.0370(2) Uani 1 1 d GU . .
H13W H 0.7269 1.7517 0.3779 0.056 Uiso 1 1 d GD . .
H23W H 0.6728 1.8151 0.3052 0.056 Uiso 1 1 d GD . .
O2W O 0.19270(9) 1.3490(5) 0.30050(4) 0.0640(1) Uani 1 1 d GU . .
H12W H 0.2365 1.3842 0.3368 0.096 Uiso 1 1 d GD . .
H22W H 0.1870 1.2416 0.3067 0.096 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 109.7 . .
O2 C7 O1 124.91(14) . .
O2 C7 C1 122.34(8) . .
O1 C7 C1 112.48(14) . .
C7 C1 C6 127.70(6) . .
C7 C1 C2 116.36(6) . .
C6 C1 C2 115.88(5) . .
C1 C2 C3 117.97(4) . .
C1 C2 H2 120.6 . .
C3 C2 H2 120.7 . .
C4 C3 C2 118.93(4) . .
C4 C3 N1 124.41(4) . .
C2 C3 N1 116.66(4) . .
C5 C4 C3 124.31(5) . .
C5 C4 H4 117.5 . .
C3 C4 H4 117.8 . .
C6 C5 C4 119.53(5) . .
C6 C5 H5 120.2 . .
C4 C5 H5 120.4 . .
C5 C6 C1 123.28(5) . .
C5 C6 H6 118.6 . .
C1 C6 H6 118.4 . .
C10 N1 C8 118.40(5) . .
C10 N1 C3 111.00(4) . .
C8 N1 C3 113.45(3) . .
C10 N1 C9 107.69(4) . .
C8 N1 C9 101.22(2) . .
C3 N1 C9 103.27(3) . .
N1 C8 H8A 109.4 . .
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 109.4 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N1 C10 H10A 109.4 . .
N1 C10 H10B 109.6 . .
H10A C10 H10B 109.5 . .
N1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C17 O11 H11 109.7 . .
O12 C17 O11 125.32(9) . .
O12 C17 C11 119.04(9) . .
O11 C17 C11 115.0(3) . .
C16 C11 C12 118.46(5) . .
C16 C11 C17 124.28(5) . .
C12 C11 C17 117.24(5) . .
C13 C12 C11 114.81(6) . .
C13 C12 H12 122.9 . .
C11 C12 H12 122.9 . .
C12 C13 C14 123.21(5) . .
C12 C13 N2 116.66(5) . .
C14 C13 N2 119.55(6) . .
C15 C14 C13 122.00(6) . .
C15 C14 H14 119.3 . .
C13 C14 H14 118.9 . .
C16 C15 C14 117.92(6) . .
C16 C15 H15 121.3 . .
C14 C15 H15 120.8 . .
C15 C16 C11 123.00(5) . .
C15 C16 H16 118.5 . .
C11 C16 H16 118.6 . .
C19 N2 C20 104.44(4) . .
C19 N2 C13 109.15(4) . .
C20 N2 C13 109.42(4) . .
C19 N2 C18 120.90(6) . .
C20 N2 C18 93.0(3) . .
C13 N2 C18 117.22(6) . .
N2 C18 H18A 109.4 . .
N2 C18 H18B 109.4 . .
H18A C18 H18B 109.5 . .
N2 C18 H18C 109.6 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N2 C19 H19A 109.6 . .
N2 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
N2 C19 H19C 109.3 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N2 C20 H20A 109.4 . .
N2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
N2 C20 H20C 109.5 . .
H20A C20 H20C 108.0 . .
H20B C20 H20C 109.5 . .
C27 O21 H21 109.7 . .
O22 C27 O21 122.65(4) . .
O22 C27 C21 127.41(4) . .
O21 C27 C21 109.22(4) . .
C22 C21 C26 122.90(6) . .
C22 C21 C27 117.80(5) . .
C26 C21 C27 118.95(4) . .
C21 C22 C23 122.76(6) . .
C21 C22 H22 119.0 . .
C23 C22 H22 119.0 . .
C22 C23 C24 119.55(5) . .
C22 C23 N3 126.45(4) . .
C24 C23 N3 113.72(4) . .
C23 C24 C25 116.77(5) . .
C23 C24 H24 121.6 . .
C25 C24 H24 121.7 . .
C24 C25 C26 119.83(5) . .
C24 C25 H25 119.9 . .
C26 C25 H25 120.0 . .
C21 C26 C25 117.46(4) . .
C21 C26 H26 121.6 . .
C25 C26 H26 121.4 . .
C29 N3 C23 120.48(4) . .
C29 N3 C28 107.13(6) . .
C23 N3 C28 110.22(4) . .
C29 N3 C30 110.61(3) . .
C23 N3 C30 105.59(3) . .
C28 N3 C30 101.14(5) . .
N3 C28 H28A 109.5 . .
N3 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
N3 C28 H28C 109.4 . .
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 109.4 . .
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 122.4(3) . .
O32 C37 C31 123.9(3) . .
O31 C37 C31 112.5(2) . .
C32 C31 C36 121.42(6) . .
C32 C31 C37 122.71(15) . .
C36 C31 C37 115.88(15) . .
C31 C32 C33 121.10(5) . .
C31 C32 H32 119.1 . .
C33 C32 H32 119.1 . .
C34 C33 C32 119.33(4) . .
C34 C33 N4 115.5(2) . .
C32 C33 N4 125.0(4) . .
C33 C34 C35 118.13(5) . .
C33 C34 H34 121.6 . .
C35 C34 H34 120.0 . .
C34 C35 C36 119.78(5) . .
C34 C35 H35 119.7 . .
C36 C35 H35 119.3 . .
C35 C36 C31 119.49(5) . .
C35 C36 H36 120.7 . .
C31 C36 H36 120.6 . .
C38 N4 C39 118.3(2) . .
C38 N4 C33 109.2(3) . .
C39 N4 C33 112.82(16) . .
C38 N4 C40 94.0(3) . .
C39 N4 C40 111.0(3) . .
C33 N4 C40 110.0(3) . .
N4 C38 H38A 109.4 . .
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 109.5 . .
N4 C39 H39B 109.4 . .
H39A C39 H39B 109.5 . .
N4 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
N4 C40 H40A 109.4 . .
N4 C40 H40B 109.4 . .
H40A C40 H40B 109.5 . .
N4 C40 H40C 109.6 . .
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 1.350(3) .
O1 H1 0.8200 .
O2 C7 1.2481(18) .
C7 C1 1.5366(17) .
C1 C6 1.4403(8) .
C1 C2 1.4355(7) .
C2 C3 1.4672(6) .
C2 H2 0.9300 .
C3 C4 1.3138(8) .
C3 N1 1.5019(6) .
C4 C5 1.3608(7) .
C4 H4 0.9300 .
C5 C6 1.3169(7) .
C5 H5 0.9300 .
C6 H6 0.9300 .
N1 C10 1.3916(6) .
N1 C8 1.4700(4) .
N1 C9 1.6358(5) .
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 1.3065(13) .
O11 H11 0.8200 .
O12 C17 1.1945(5) .
C17 C11 1.4506(7) .
C11 C16 1.3778(9) .
C11 C12 1.4615(8) .
C12 C13 1.4066(9) .
C12 H12 0.9300 .
C13 C14 1.2946(9) .
C13 N2 1.5168(7) .
C14 C15 1.3984(8) .
C14 H14 0.9300 .
C15 C16 1.330(6) .
C15 H15 0.9300 .
C16 H16 0.9300 .
N2 C19 1.5203(7) .
N2 C20 1.4429(6) .
N2 C18 1.4619(19) .
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 0.9700 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
O21 C27 1.3523(5) .
O21 H21 0.8200 .
O22 C27 1.2451(12) .
C27 C21 1.470(6) .
C21 C22 1.3267(8) .
C21 C26 1.3464(8) .
C22 C23 1.2932(8) .
C22 H22 0.9300 .
C23 C24 1.4455(8) .
C23 N3 1.5209(5) .
C24 C25 1.4021(7) .
C24 H24 0.9300 .
C25 C26 1.4110(6) .
C25 H25 0.9300 .
C26 H26 0.9300 .
N3 C29 1.4054(6) .
N3 C28 1.4876(12) .
N3 C30 1.6315(4) .
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 1.343(3) .
O31 H31 0.8200 .
O32 C37 1.2424(6) .
C37 C31 1.518(3) .
C31 C32 1.3624(7) .
C31 C36 1.3655(9) .
C32 C33 1.3631(7) .
C32 H32 0.9300 .
C33 C34 1.4327(8) .
C33 N4 1.4941(7) .
C34 C35 1.4080(7) .
C34 H34 0.9300 .
C35 C36 1.40(5) .
C35 H35 0.9300 .
C36 H36 0.9300 .
N4 C38 1.550(4) .
N4 C39 1.560(4) .
N4 C40 1.490(5) .
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 0.8537 .
O4W H24W 0.8550 .
O1W H11W 0.8539 .
O1W H21W 0.8531 .
O3W H13W 0.8536 .
O3W H23W 0.8546 .
O2W H12W 0.8538 .
O2W H22W 0.8539 .
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 179.26(8) . . . .
O1 C7 C1 C6 4.95(16) . . . .
O2 C7 C1 C2 -3.94(14) . . . .
O1 C7 C1 C2 -178.25(11) . . . .
C7 C1 C2 C3 -177.93(6) . . . .
C6 C1 C2 C3 -0.74(6) . . . .
C1 C2 C3 C4 -0.29(6) . . . .
C1 C2 C3 N1 179.78(4) . . . .
C2 C3 C4 C5 2.76(7) . . . .
N1 C3 C4 C5 -177.32(4) . . . .
C3 C4 C5 C6 -4.11(8) . . . .
C4 C5 C6 C1 2.88(8) . . . .
C7 C1 C6 C5 176.25(8) . . . .
C2 C1 C6 C5 -0.57(8) . . . .
C4 C3 N1 C10 58.71(7) . . . .
C2 C3 N1 C10 -121.36(6) . . . .
C4 C3 N1 C8 -165.10(4) . . . .
C2 C3 N1 C8 14.83(5) . . . .
C4 C3 N1 C9 -56.43(5) . . . .
C2 C3 N1 C9 123.50(4) . . . .
O12 C17 C11 C16 10.37(7) . . . .
O11 C17 C11 C16 -178.35(4) . . . .
O12 C17 C11 C12 -171.36(4) . . . .
O11 C17 C11 C12 -0.07(6) . . . .
C16 C11 C12 C13 2.66(7) . . . .
C17 C11 C12 C13 -175.72(4) . . . .
C11 C12 C13 C14 -5.83(8) . . . .
C11 C12 C13 N2 -177.02(4) . . . .
C12 C13 C14 C15 2.36(9) . . . .
N2 C13 C14 C15 173.30(5) . . . .
C13 C14 C15 C16 4.64(8) . . . .
C14 C15 C16 C11 -7.83(8) . . . .
C12 C11 C16 C15 4.13(8) . . . .
C17 C11 C16 C15 -177.62(5) . . . .
C12 C13 N2 C19 124.83(5) . . . .
C14 C13 N2 C19 -46.70(6) . . . .
C12 C13 N2 C20 -121.45(5) . . . .
C14 C13 N2 C20 67.02(6) . . . .
C12 C13 N2 C18 -17.36(8) . . . .
C14 C13 N2 C18 171.11(7) . . . .
O22 C27 C21 C22 -14.37(7) . . . .
O21 C27 C21 C22 175.27(4) . . . .
O22 C27 C21 C26 172.16(4) . . . .
O21 C27 C21 C26 1.80(6) . . . .
C26 C21 C22 C23 -2.95(8) . . . .
C27 C21 C22 C23 -176.15(5) . . . .
C21 C22 C23 C24 -5.10(8) . . . .
C21 C22 C23 N3 -178.58(5) . . . .
C22 C23 C24 C25 9.20(7) . . . .
N3 C23 C24 C25 -176.52(4) . . . .
C23 C24 C25 C26 -5.79(7) . . . .
C22 C21 C26 C25 6.27(7) . . . .
C27 C21 C26 C25 179.39(4) . . . .
C24 C25 C26 C21 -1.52(7) . . . .
C22 C23 N3 C29 -166.50(4) . . . .
C24 C23 N3 C29 19.69(5) . . . .
C22 C23 N3 C28 -40.98(7) . . . .
C24 C23 N3 C28 145.21(6) . . . .
C22 C23 N3 C30 67.47(5) . . . .
C24 C23 N3 C30 -106.34(4) . . . .
O32 C37 C31 C32 -176.1(3) . . . .
O31 C37 C31 C32 16.4(4) . . . .
O32 C37 C31 C36 3.9(5) . . . .
O31 C37 C31 C36 -163.6(2) . . . .
C36 C31 C32 C33 -6.35(7) . . . .
C37 C31 C32 C33 173.6(2) . . . .
C31 C32 C33 C34 8.57(7) . . . .
C31 C32 C33 N4 -178.39(4) . . . .
C32 C33 C34 C35 -2.91(6) . . . .
N4 C33 C34 C35 -176.58(5) . . . .
C33 C34 C35 C36 -4.89(6) . . . .
C34 C35 C36 C31 7.26(7) . . . .
C32 C31 C36 C35 -1.73(8) . . . .
C37 C31 C36 C35 178.3(2) . . . .
C34 C33 N4 C38 -171.77(8) . . . .
C32 C33 N4 C38 14.95(11) . . . .
C34 C33 N4 C39 54.5(3) . . . .
C32 C33 N4 C39 -118.8(3) . . . .
C34 C33 N4 C40 -69.9(3) . . . .
C32 C33 N4 C40 116.8(3) . . . .
