#------------------------------------------------------------------------------
#$Date: 2020-08-05 04:47:01 +0300 (Wed, 05 Aug 2020) $
#$Revision: 254819 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/09/7240984.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_7240984
loop_
_publ_author_name
'Cruz-Cabeza, A. J.'
'Taylor, E.'
'Sugden, I. J.'
'Bowskill, D. H.'
'Wright, S. E.'
'Abdullahi, H.'
'Tulegenov, D.'
'Sadiq, G.'
'Davey, R. J.'
_publ_section_title
;
 Can solvated intermediates inform us about nucleation pathways? The case
 of β-pABA
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00970A
_journal_year                    2020
_chemical_formula_sum            'C18 H22 N2 O6'
_chemical_formula_weight         362.37
_chemical_name_systematic        '4-aminobenzoic acid dioxane solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.194(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   22.4397(9)
_cell_length_b                   20.5326(7)
_cell_length_c                   11.9083(4)
_cell_measurement_reflns_used    2106
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.91
_cell_measurement_theta_min      4.31
_cell_volume                     5294.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10342
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.364
_diffrn_reflns_theta_min         2.040
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.77675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             2304
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dioxane/Water'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         10342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0801
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0818P)²+6.4938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6217
_reflns_number_total             10342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00970a2.cif
_cod_data_source_block           s4474mat
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240984
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.807
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16898(19) 0.5876(2) 0.2727(4) 0.0291(9) Uani 1 1 d . . . . .
C2 C 0.16710(18) 0.6545(2) 0.2272(4) 0.0273(8) Uani 1 1 d . . . . .
C3 C 0.14257(19) 0.7058(2) 0.2781(4) 0.0286(9) Uani 1 1 d . . . . .
H3 H 0.1261 0.6973 0.3425 0.034 Uiso 1 1 calc R U . . .
C4 C 0.14184(19) 0.7686(2) 0.2366(4) 0.0301(9) Uani 1 1 d . . . . .
H4 H 0.1243 0.8026 0.2715 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1669(2) 0.7822(2) 0.1428(4) 0.0313(9) Uani 1 1 d . . . . .
C6 C 0.1914(2) 0.7305(2) 0.0907(4) 0.0310(9) Uani 1 1 d . . . . .
H6 H 0.2080 0.7387 0.0265 0.037 Uiso 1 1 calc R U . . .
C7 C 0.19118(19) 0.6679(2) 0.1332(4) 0.0285(9) Uani 1 1 d . . . . .
H7 H 0.2078 0.6334 0.0976 0.034 Uiso 1 1 calc R U . . .
C8 C 0.17400(19) 0.4124(2) 0.3960(4) 0.0286(9) Uani 1 1 d . . . . .
C9 C 0.17162(18) 0.3458(2) 0.4380(3) 0.0257(8) Uani 1 1 d . . . . .
C10 C 0.19216(18) 0.2931(2) 0.3841(4) 0.0280(9) Uani 1 1 d . . . . .
H10 H 0.2086 0.3005 0.3194 0.034 Uiso 1 1 calc R U . . .
C11 C 0.18894(19) 0.2303(2) 0.4235(4) 0.0300(9) Uani 1 1 d . . . . .
H11 H 0.2034 0.1951 0.3860 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1645(2) 0.2179(2) 0.5184(4) 0.0314(9) Uani 1 1 d . . . . .
C13 C 0.1441(2) 0.2708(2) 0.5726(4) 0.0317(9) Uani 1 1 d . . . . .
H13 H 0.1277 0.2635 0.6374 0.038 Uiso 1 1 calc R U . . .
C14 C 0.14767(19) 0.3336(2) 0.5329(4) 0.0289(9) Uani 1 1 d . . . . .
H14 H 0.1336 0.3689 0.5707 0.035 Uiso 1 1 calc R U . . .
C15 C 0.32395(19) 0.0865(2) 0.2181(3) 0.0299(9) Uani 1 1 d . . . . .
C16 C 0.32702(19) 0.1530(2) 0.2630(4) 0.0293(9) Uani 1 1 d . . . . .
C17 C 0.30687(19) 0.2062(2) 0.1891(4) 0.0302(9) Uani 1 1 d . . . . .
H17 H 0.2896 0.1992 0.1082 0.036 Uiso 1 1 calc R U . . .
C18 C 0.31197(19) 0.2684(2) 0.2329(4) 0.0307(9) Uani 1 1 d . . . . .
H18 H 0.2977 0.3038 0.1817 0.037 Uiso 1 1 calc R U . . .
C19 C 0.33784(19) 0.2809(2) 0.3517(4) 0.0325(9) Uani 1 1 d . . . . .
C20 C 0.3575(2) 0.2273(2) 0.4264(4) 0.0333(9) Uani 1 1 d . . . . .
H20 H 0.3745 0.2341 0.5074 0.040 Uiso 1 1 calc R U . . .
C21 C 0.35191(19) 0.1652(2) 0.3817(4) 0.0320(9) Uani 1 1 d . . . . .
H21 H 0.3654 0.1296 0.4328 0.038 Uiso 1 1 calc R U . . .
C22 C 0.6761(2) 0.4105(2) 0.3934(3) 0.0309(9) Uani 1 1 d . . . . .
C23 C 0.67269(19) 0.3441(2) 0.4361(4) 0.0287(9) Uani 1 1 d . . . . .
C24 C 0.69607(19) 0.3297(2) 0.5537(4) 0.0307(9) Uani 1 1 d . . . . .
H24 H 0.7133 0.3637 0.6063 0.037 Uiso 1 1 calc R U . . .
C25 C 0.69483(19) 0.2675(2) 0.5955(3) 0.0300(9) Uani 1 1 d . . . . .
H25 H 0.7111 0.2590 0.6762 0.036 Uiso 1 1 calc R U . . .
C26 C 0.6698(2) 0.2165(2) 0.5199(4) 0.0314(9) Uani 1 1 d . . . . .
C27 C 0.6455(2) 0.2312(2) 0.4015(4) 0.0325(9) Uani 1 1 d . . . . .
H27 H 0.6273 0.1975 0.3491 0.039 Uiso 1 1 calc R U . . .
C28 C 0.6474(2) 0.2930(2) 0.3600(4) 0.0297(9) Uani 1 1 d . . . . .
H28 H 0.6316 0.3015 0.2793 0.036 Uiso 1 1 calc R U . . .
C29 C 0.0045(2) 0.4113(2) 0.0539(4) 0.0332(9) Uani 1 1 d . . . . .
C30 C 0.00436(19) 0.3447(2) 0.0982(4) 0.0303(9) Uani 1 1 d . . . . .
C31 C 0.0297(2) 0.3308(2) 0.2162(4) 0.0338(10) Uani 1 1 d . . . . .
H31 H 0.0469 0.3651 0.2681 0.041 Uiso 1 1 calc R U . . .
C32 C 0.0301(2) 0.2687(3) 0.2582(4) 0.0343(10) Uani 1 1 d . . . . .
H32 H 0.0474 0.2603 0.3386 0.041 Uiso 1 1 calc R U . . .
C33 C 0.0049(2) 0.2172(2) 0.1829(4) 0.0342(10) Uani 1 1 d . . . . .
C34 C -0.0212(2) 0.2309(2) 0.0650(4) 0.0336(10) Uani 1 1 d . . . . .
H34 H -0.0386 0.1966 0.0131 0.040 Uiso 1 1 calc R U . . .
C35 C -0.0218(2) 0.2937(2) 0.0238(4) 0.0337(10) Uani 1 1 d . . . . .
H35 H -0.0403 0.3024 -0.0561 0.040 Uiso 1 1 calc R U . . .
C36 C 0.4962(2) 0.0891(2) 0.0484(4) 0.0340(10) Uani 1 1 d . . . . .
C37 C 0.49713(19) 0.1558(2) 0.0925(4) 0.0307(9) Uani 1 1 d . . . . .
C38 C 0.47103(19) 0.1704(2) 0.1846(4) 0.0330(10) Uani 1 1 d . . . . .
H38 H 0.4525 0.1367 0.2185 0.040 Uiso 1 1 calc R U . . .
C39 C 0.4721(2) 0.2332(2) 0.2264(4) 0.0340(10) Uani 1 1 d . . . . .
H39 H 0.4546 0.2422 0.2892 0.041 Uiso 1 1 calc R U . . .
C40 C 0.4985(2) 0.2833(2) 0.1776(4) 0.0326(9) Uani 1 1 d . . . . .
C41 C 0.52489(19) 0.2687(2) 0.0851(4) 0.0327(9) Uani 1 1 d . . . . .
H41 H 0.5430 0.3025 0.0509 0.039 Uiso 1 1 calc R U . . .
C42 C 0.52474(19) 0.2058(2) 0.0439(4) 0.0309(9) Uani 1 1 d . . . . .
H42 H 0.5434 0.1965 -0.0173 0.037 Uiso 1 1 calc R U . . .
C43 C 0.3306(2) 0.4429(2) 0.1267(4) 0.0396(11) Uani 1 1 d . . . . .
H43A H 0.3011 0.4121 0.0774 0.048 Uiso 1 1 calc R U . . .
H43B H 0.3722 0.4230 0.1446 0.048 Uiso 1 1 calc R U . . .
C44 C 0.3308(3) 0.5053(2) 0.0615(4) 0.0462(12) Uani 1 1 d . . . . .
H44A H 0.3447 0.4966 -0.0094 0.055 Uiso 1 1 calc R U . . .
H44B H 0.2884 0.5230 0.0371 0.055 Uiso 1 1 calc R U . . .
C45 C 0.3532(2) 0.5634(2) 0.2358(4) 0.0399(11) Uani 1 1 d . . . . .
H45A H 0.3112 0.5825 0.2175 0.048 Uiso 1 1 calc R U . . .
H45B H 0.3822 0.5947 0.2850 0.048 Uiso 1 1 calc R U . . .
C46 C 0.3539(3) 0.5006(3) 0.3008(5) 0.0516(14) Uani 1 1 d . . . . .
H46A H 0.3964 0.4831 0.3235 0.062 Uiso 1 1 calc R U . . .
H46B H 0.3409 0.5090 0.3728 0.062 Uiso 1 1 calc R U . . .
C47 C 0.1781(3) 0.5045(3) 0.7303(5) 0.0462(12) Uani 1 1 d . . . . .
H47A H 0.2204 0.5227 0.7541 0.055 Uiso 1 1 calc R U . . .
H47B H 0.1680 0.4951 0.6458 0.055 Uiso 1 1 calc R U . . .
C48 C 0.1757(3) 0.4423(3) 0.7959(4) 0.0420(11) Uani 1 1 d . . . . .
H48A H 0.1341 0.4226 0.7685 0.050 Uiso 1 1 calc R U . . .
H48B H 0.2062 0.4110 0.7808 0.050 Uiso 1 1 calc R U . . .
C49 C 0.1454(3) 0.5015(3) 0.9394(4) 0.0476(13) Uani 1 1 d . . . . .
H49A H 0.1549 0.5106 1.0239 0.057 Uiso 1 1 calc R U . . .
H49B H 0.1031 0.4834 0.9143 0.057 Uiso 1 1 calc R U . . .
C50 C 0.1487(3) 0.5636(3) 0.8746(4) 0.0429(12) Uani 1 1 d . . . . .
H50A H 0.1186 0.5954 0.8900 0.051 Uiso 1 1 calc R U . . .
H50B H 0.1905 0.5827 0.9020 0.051 Uiso 1 1 calc R U . . .
C51 C 0.4976(2) 0.5613(3) 1.0463(4) 0.0392(10) Uani 1 1 d . . . . .
H51A H 0.4770 0.5936 1.0852 0.047 Uiso 1 1 calc R U . . .
H51B H 0.5365 0.5809 1.0381 0.047 Uiso 1 1 calc R U . . .
C52 C 0.4881(2) 0.4986(3) 0.8801(4) 0.0411(11) Uani 1 1 d . . . . .
H52A H 0.5267 0.5164 0.8672 0.049 Uiso 1 1 calc R U . . .
H52B H 0.4603 0.4871 0.8034 0.049 Uiso 1 1 calc R U . . .
C53 C 0.0036(2) 0.5614(3) 0.5515(4) 0.0404(11) Uani 1 1 d . . . . .
H53A H -0.0364 0.5812 0.5107 0.048 Uiso 1 1 calc R U . . .
H53B H 0.0262 0.5929 0.6102 0.048 Uiso 1 1 calc R U . . .
C54 C 0.0078(2) 0.4997(3) 0.3886(4) 0.0397(11) Uani 1 1 d . . . . .
H54A H 0.0338 0.4894 0.3354 0.048 Uiso 1 1 calc R U . . .
H54B H -0.0321 0.5170 0.3413 0.048 Uiso 1 1 calc R U . . .
N1 N 0.1676(2) 0.8446(2) 0.1026(4) 0.0438(10) Uani 1 1 d . . . . .
H1A H 0.153(3) 0.875(3) 0.135(5) 0.053 Uiso 1 1 d . U . . .
H1B H 0.184(3) 0.851(3) 0.035(5) 0.053 Uiso 1 1 d . U . . .
N2 N 0.1609(2) 0.1558(2) 0.5572(4) 0.0448(10) Uani 1 1 d . . . . .
H2A H 0.1456 0.1487 0.6170 0.054 Uiso 1 1 calc R U . . .
H2B H 0.1739 0.1230 0.5224 0.054 Uiso 1 1 calc R U . . .
N3 N 0.3441(2) 0.3429(2) 0.3940(4) 0.0445(10) Uani 1 1 d . . . . .
H3A H 0.3318 0.3760 0.3467 0.053 Uiso 1 1 calc R U . . .
H3B H 0.3604 0.3498 0.4687 0.053 Uiso 1 1 calc R U . . .
N4 N 0.6699(2) 0.1538(2) 0.5591(4) 0.0440(10) Uani 1 1 d . . . . .
H4A H 0.6859 0.1449 0.6331 0.053 Uiso 1 1 calc R U . . .
H4B H 0.6539 0.1224 0.5102 0.053 Uiso 1 1 calc R U . . .
N5 N 0.0070(2) 0.1542(2) 0.2221(4) 0.0457(10) Uani 1 1 d . . . . .
H5C H 0.014(3) 0.150(3) 0.294(6) 0.055 Uiso 1 1 d . U . . .
H5B H -0.021(3) 0.131(3) 0.178(5) 0.055 Uiso 1 1 d . U . . .
N6 N 0.4984(2) 0.3465(2) 0.2150(4) 0.0448(10) Uani 1 1 d . . . . .
H6A H 0.4814 0.3562 0.2715 0.054 Uiso 1 1 calc R U . . .
H6B H 0.5155 0.3773 0.1825 0.054 Uiso 1 1 calc R U . . .
O1 O 0.18989(17) 0.54187(16) 0.2277(3) 0.0408(8) Uani 1 1 d . . . . .
O2 O 0.14793(17) 0.58046(17) 0.3643(3) 0.0402(8) Uani 1 1 d . . . . .
H2 H 0.1519 0.5414 0.3863 0.060 Uiso 1 1 calc R U . . .
O4 O 0.19400(18) 0.41884(16) 0.3031(3) 0.0413(8) Uani 1 1 d . . . . .
H4C H 0.1935 0.4584 0.2849 0.062 Uiso 1 1 calc R U . . .
O3 O 0.15724(17) 0.46006(16) 0.4445(3) 0.0389(8) Uani 1 1 d . . . . .
O6 O 0.30466(18) 0.07868(17) 0.1062(3) 0.0429(8) Uani 1 1 d . . . . .
H6C H 0.3029 0.0387 0.0904 0.064 Uiso 1 1 calc R U . . .
O5 O 0.33874(18) 0.03939(16) 0.2873(3) 0.0420(8) Uani 1 1 d . . . . .
O7 O 0.69797(18) 0.45593(17) 0.4608(3) 0.0439(8) Uani 1 1 d . . . . .
O8 O 0.65526(19) 0.41933(17) 0.2814(3) 0.0443(8) Uani 1 1 d . . . . .
H8 H 0.6540 0.4594 0.2666 0.066 Uiso 1 1 calc R U . . .
O9 O -0.01879(18) 0.42281(18) -0.0530(3) 0.0455(9) Uani 1 1 d . . . . .
O10 O 0.02793(19) 0.45623(18) 0.1263(3) 0.0474(9) Uani 1 1 d . . . . .
H10A H 0.0259 0.4919 0.0910 0.071 Uiso 1 1 calc R U . . .
O11 O 0.51980(19) 0.07665(18) -0.0350(3) 0.0480(9) Uani 1 1 d . . . . .
O12 O 0.47120(19) 0.04479(18) 0.0972(3) 0.0483(9) Uani 1 1 d . . . . .
H12 H 0.4732 0.0088 0.0649 0.072 Uiso 1 1 calc R U . . .
O13 O 0.37059(15) 0.55225(16) 0.1311(3) 0.0367(7) Uani 1 1 d . . . . .
O14 O 0.31361(18) 0.45389(18) 0.2315(3) 0.0490(9) Uani 1 1 d . . . . .
O15 O 0.18871(16) 0.45489(17) 0.9175(3) 0.0424(8) Uani 1 1 d . . . . .
O16 O 0.13528(16) 0.55104(17) 0.7527(3) 0.0413(8) Uani 1 1 d . . . . .
O17 O 0.45901(16) 0.54729(17) 0.9350(3) 0.0418(8) Uani 1 1 d . . . . .
O18 O 0.03815(17) 0.54885(19) 0.4706(3) 0.0473(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 C1 O2 122.7(4) . . ?
O1 C1 C2 121.8(4) . . ?
O2 C1 C2 115.5(4) . . ?
C7 C2 C3 118.6(4) . . ?
C7 C2 C1 120.1(4) . . ?
C3 C2 C1 121.3(4) . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.6(4) . . ?
N1 C5 C6 120.5(4) . . ?
C4 C5 C6 118.8(4) . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O3 C8 O4 121.8(4) . . ?
O3 C8 C9 122.3(4) . . ?
O4 C8 C9 115.9(4) . . ?
C10 C9 C14 118.4(4) . . ?
C10 C9 C8 121.5(4) . . ?
C14 C9 C8 120.1(4) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
N2 C12 C13 120.9(4) . . ?
N2 C12 C11 120.8(4) . . ?
C13 C12 C11 118.3(4) . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 120.9(4) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
O5 C15 O6 122.5(4) . . ?
O5 C15 C16 120.0(4) . . ?
O6 C15 C16 117.4(4) . . ?
C21 C16 C17 118.2(4) . . ?
C21 C16 C15 120.3(4) . . ?
C17 C16 C15 121.5(4) . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.6(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
N3 C19 C18 121.2(4) . . ?
N3 C19 C20 120.7(4) . . ?
C18 C19 C20 118.1(4) . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C16 122.0(4) . . ?
C20 C21 H21 119.0 . . ?
C16 C21 H21 119.0 . . ?
O7 C22 O8 122.0(4) . . ?
O7 C22 C23 121.4(4) . . ?
O8 C22 C23 116.5(4) . . ?
C24 C23 C28 118.2(4) . . ?
C24 C23 C22 120.5(4) . . ?
C28 C23 C22 121.4(4) . . ?
C25 C24 C23 121.6(4) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 120.4(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
N4 C26 C25 121.4(4) . . ?
N4 C26 C27 120.6(4) . . ?
C25 C26 C27 118.0(4) . . ?
C28 C27 C26 121.5(4) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C23 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
O9 C29 O10 122.2(5) . . ?
O9 C29 C30 119.8(4) . . ?
O10 C29 C30 118.0(4) . . ?
C31 C30 C35 118.4(4) . . ?
C31 C30 C29 120.8(4) . . ?
C35 C30 C29 120.8(4) . . ?
C32 C31 C30 121.2(4) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C33 120.3(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
N5 C33 C34 119.8(5) . . ?
N5 C33 C32 121.4(5) . . ?
C34 C33 C32 118.8(5) . . ?
C35 C34 C33 120.4(5) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C30 120.8(4) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
O11 C36 O12 122.1(4) . . ?
O11 C36 C37 120.0(4) . . ?
O12 C36 C37 117.9(4) . . ?
C42 C37 C38 119.2(4) . . ?
C42 C37 C36 120.2(4) . . ?
C38 C37 C36 120.6(4) . . ?
C39 C38 C37 120.6(4) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 120.8(4) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
N6 C40 C39 121.9(4) . . ?
N6 C40 C41 119.4(4) . . ?
C39 C40 C41 118.7(4) . . ?
C42 C41 C40 120.9(4) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C41 C42 C37 119.9(4) . . ?
C41 C42 H42 120.1 . . ?
C37 C42 H42 120.1 . . ?
O14 C43 C44 111.0(4) . . ?
O14 C43 H43A 109.4 . . ?
C44 C43 H43A 109.4 . . ?
O14 C43 H43B 109.4 . . ?
C44 C43 H43B 109.4 . . ?
H43A C43 H43B 108.0 . . ?
O13 C44 C43 111.4(4) . . ?
O13 C44 H44A 109.4 . . ?
C43 C44 H44A 109.4 . . ?
O13 C44 H44B 109.4 . . ?
C43 C44 H44B 109.4 . . ?
H44A C44 H44B 108.0 . . ?
O13 C45 C46 110.3(4) . . ?
O13 C45 H45A 109.6 . . ?
C46 C45 H45A 109.6 . . ?
O13 C45 H45B 109.6 . . ?
C46 C45 H45B 109.6 . . ?
H45A C45 H45B 108.1 . . ?
O14 C46 C45 111.1(5) . . ?
O14 C46 H46A 109.4 . . ?
C45 C46 H46A 109.4 . . ?
O14 C46 H46B 109.4 . . ?
C45 C46 H46B 109.4 . . ?
H46A C46 H46B 108.0 . . ?
O16 C47 C48 110.7(4) . . ?
O16 C47 H47A 109.5 . . ?
C48 C47 H47A 109.5 . . ?
O16 C47 H47B 109.5 . . ?
C48 C47 H47B 109.5 . . ?
H47A C47 H47B 108.1 . . ?
O15 C48 C47 110.4(4) . . ?
O15 C48 H48A 109.6 . . ?
C47 C48 H48A 109.6 . . ?
O15 C48 H48B 109.6 . . ?
C47 C48 H48B 109.6 . . ?
H48A C48 H48B 108.1 . . ?
O15 C49 C50 110.2(4) . . ?
O15 C49 H49A 109.6 . . ?
C50 C49 H49A 109.6 . . ?
O15 C49 H49B 109.6 . . ?
C50 C49 H49B 109.6 . . ?
H49A C49 H49B 108.1 . . ?
O16 C50 C49 110.1(4) . . ?
O16 C50 H50A 109.6 . . ?
C49 C50 H50A 109.6 . . ?
O16 C50 H50B 109.6 . . ?
C49 C50 H50B 109.6 . . ?
H50A C50 H50B 108.2 . . ?
O17 C51 C52 111.6(4) . 3_667 ?
O17 C51 H51A 109.3 . . ?
C52 C51 H51A 109.3 3_667 . ?
O17 C51 H51B 109.3 . . ?
C52 C51 H51B 109.3 3_667 . ?
H51A C51 H51B 108.0 . . ?
O17 C52 C51 111.1(4) . 3_667 ?
O17 C52 H52A 109.4 . . ?
C51 C52 H52A 109.4 3_667 . ?
O17 C52 H52B 109.4 . . ?
C51 C52 H52B 109.4 3_667 . ?
H52A C52 H52B 108.0 . . ?
O18 C53 C54 111.5(4) . 3_566 ?
O18 C53 H53A 109.3 . . ?
C54 C53 H53A 109.3 3_566 . ?
O18 C53 H53B 109.3 . . ?
C54 C53 H53B 109.3 3_566 . ?
H53A C53 H53B 108.0 . . ?
O18 C54 C53 111.9(4) . 3_566 ?
O18 C54 H54A 109.2 . . ?
C53 C54 H54A 109.2 3_566 . ?
O18 C54 H54B 109.2 . . ?
C53 C54 H54B 109.2 3_566 . ?
H54A C54 H54B 107.9 . . ?
C5 N1 H1A 120(4) . . ?
C5 N1 H1B 117(4) . . ?
H1A N1 H1B 123(5) . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C19 N3 H3A 120.0 . . ?
C19 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C26 N4 H4A 120.0 . . ?
C26 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C33 N5 H5C 116(5) . . ?
C33 N5 H5B 112(4) . . ?
H5C N5 H5B 118(6) . . ?
C40 N6 H6A 120.0 . . ?
C40 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C1 O2 H2 109.5 . . ?
C8 O4 H4C 109.5 . . ?
C15 O6 H6C 109.5 . . ?
C22 O8 H8 109.5 . . ?
C29 O10 H10A 109.5 . . ?
C36 O12 H12 109.5 . . ?
C45 O13 C44 110.2(4) . . ?
C43 O14 C46 110.0(4) . . ?
C48 O15 C49 109.7(4) . . ?
C47 O16 C50 109.8(4) . . ?
C51 O17 C52 109.2(4) . . ?
C53 O18 C54 110.1(4) . . ?
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 O1 1.233(5) . ?
C1 O2 1.305(5) . ?
C1 C2 1.474(6) . ?
C2 C7 1.392(6) . ?
C2 C3 1.399(6) . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.369(6) . ?
C5 C6 1.412(6) . ?
C6 C7 1.381(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O3 1.244(5) . ?
C8 O4 1.305(5) . ?
C8 C9 1.461(6) . ?
C9 C10 1.397(6) . ?
C9 C14 1.396(6) . ?
C10 C11 1.380(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(6) . ?
C11 H11 0.9500 . ?
C12 N2 1.364(6) . ?
C12 C13 1.401(6) . ?
C13 C14 1.382(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O5 1.257(5) . ?
C15 O6 1.299(5) . ?
C15 C16 1.463(6) . ?
C16 C21 1.399(6) . ?
C16 C17 1.401(6) . ?
C17 C18 1.372(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(6) . ?
C18 H18 0.9500 . ?
C19 N3 1.363(6) . ?
C19 C20 1.411(7) . ?
C20 C21 1.373(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O7 1.245(5) . ?
C22 O8 1.305(5) . ?
C22 C23 1.464(6) . ?
C23 C24 1.393(6) . ?
C23 C28 1.404(6) . ?
C24 C25 1.374(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(6) . ?
C25 H25 0.9500 . ?
C26 N4 1.369(6) . ?
C26 C27 1.405(6) . ?
C27 C28 1.367(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 O9 1.266(5) . ?
C29 O10 1.278(6) . ?
C29 C30 1.466(7) . ?
C30 C31 1.400(6) . ?
C30 C35 1.398(6) . ?
C31 C32 1.370(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.404(7) . ?
C32 H32 0.9500 . ?
C33 N5 1.372(7) . ?
C33 C34 1.401(6) . ?
C34 C35 1.378(7) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 O11 1.268(5) . ?
C36 O12 1.285(5) . ?
C36 C37 1.465(6) . ?
C37 C42 1.400(6) . ?
C37 C38 1.405(6) . ?
C38 C39 1.380(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.388(7) . ?
C39 H39 0.9500 . ?
C40 N6 1.372(6) . ?
C40 C41 1.414(6) . ?
C41 C42 1.380(6) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 O14 1.414(6) . ?
C43 C44 1.500(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 O13 1.422(6) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 O13 1.420(5) . ?
C45 C46 1.501(7) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 O14 1.424(7) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 O16 1.429(6) . ?
C47 C48 1.504(7) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 O15 1.423(6) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 O15 1.436(6) . ?
C49 C50 1.503(7) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 O16 1.426(6) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 O17 1.409(6) . ?
C51 C52 1.495(7) 3_667 ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 O17 1.441(6) . ?
C52 C51 1.496(7) 3_667 ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 O18 1.409(6) . ?
C53 C54 1.497(7) 3_566 ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 O18 1.444(6) . ?
C54 C53 1.497(7) 3_566 ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
N1 H1A 0.84(6) . ?
N1 H1B 0.98(6) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 H5C 0.83(6) . ?
N5 H5B 0.86(6) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
O2 H2 0.8400 . ?
O4 H4C 0.8400 . ?
O6 H6C 0.8400 . ?
O8 H8 0.8400 . ?
O10 H10A 0.8400 . ?
O12 H12 0.8400 . ?
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
C44 H44A O5 0.99 2.50 3.442(6) 158.6 4_565
C46 H46B O7 0.99 2.47 3.454(6) 172.0 3_666
C47 H47B O3 0.99 2.45 3.435(6) 170.9 .
C49 H49A O1 0.99 2.43 3.417(6) 172.1 1_556
C52 H52B O12 0.99 2.61 3.409(6) 137.3 4_566
C54 H54A O10 0.99 2.55 3.392(6) 142.6 .
N1 H1A O16 0.84(6) 2.17(6) 2.999(6) 166(6) 4_575
N1 H1B O2 0.98(6) 2.43(6) 3.155(5) 130(4) 4_575
N2 H2A O4 0.88 2.60 3.216(5) 128.0 4_566
N2 H2B O15 0.88 2.11 2.979(6) 169.5 4_565
N3 H3A O14 0.88 2.08 2.952(6) 172.9 .
N4 H4B O13 0.88 2.17 3.036(5) 167.1 2_645
N4 H4A O8 0.88 2.44 3.135(5) 135.9 4_566
N5 H5C O9 0.83(6) 2.60(6) 3.289(6) 140(6) 4_566
N5 H5B O2 0.86(6) 2.94(6) 3.682(6) 146(5) 2_545
N5 H5B O18 0.86(6) 2.39(7) 3.123(7) 143(5) 2_545
N6 H6A O11 0.88 2.63 3.291(6) 132.9 4_566
N6 H6B O17 0.88 2.26 3.123(6) 167.3 3_666
O2 H2 O3 0.84 1.80 2.639(5) 174.4 .
O4 H4C O1 0.84 1.84 2.675(5) 173.5 .
O6 H6C O7 0.84 1.80 2.640(5) 172.3 2_645
O8 H8 O5 0.84 1.79 2.612(5) 166.9 2_655
O10 H10A O9 0.84 1.80 2.622(5) 163.9 3_565
O12 H12 O11 0.84 1.81 2.624(5) 164.4 3_655
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
O1 C1 C2 C7 -2.1(7) . . . . ?
O2 C1 C2 C7 176.9(4) . . . . ?
O1 C1 C2 C3 179.2(4) . . . . ?
O2 C1 C2 C3 -1.7(6) . . . . ?
C7 C2 C3 C4 0.2(6) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 N1 -178.5(4) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
N1 C5 C6 C7 179.1(4) . . . . ?
C4 C5 C6 C7 -0.9(7) . . . . ?
C5 C6 C7 C2 0.0(7) . . . . ?
C3 C2 C7 C6 0.3(6) . . . . ?
C1 C2 C7 C6 -178.4(4) . . . . ?
O3 C8 C9 C10 -178.3(4) . . . . ?
O4 C8 C9 C10 2.7(6) . . . . ?
O3 C8 C9 C14 2.6(7) . . . . ?
O4 C8 C9 C14 -176.5(4) . . . . ?
C14 C9 C10 C11 0.0(6) . . . . ?
C8 C9 C10 C11 -179.1(4) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 N2 179.6(4) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
N2 C12 C13 C14 -179.8(4) . . . . ?
C11 C12 C13 C14 0.5(7) . . . . ?
C12 C13 C14 C9 0.0(7) . . . . ?
C10 C9 C14 C13 -0.2(6) . . . . ?
C8 C9 C14 C13 178.9(4) . . . . ?
O5 C15 C16 C21 6.1(6) . . . . ?
O6 C15 C16 C21 -175.0(4) . . . . ?
O5 C15 C16 C17 -175.5(4) . . . . ?
O6 C15 C16 C17 3.4(6) . . . . ?
C21 C16 C17 C18 0.4(6) . . . . ?
C15 C16 C17 C18 -178.0(4) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C17 C18 C19 N3 178.4(4) . . . . ?
C17 C18 C19 C20 -1.4(6) . . . . ?
N3 C19 C20 C21 -178.7(4) . . . . ?
C18 C19 C20 C21 1.1(6) . . . . ?
C19 C20 C21 C16 -0.1(6) . . . . ?
C17 C16 C21 C20 -0.6(6) . . . . ?
C15 C16 C21 C20 177.8(4) . . . . ?
O7 C22 C23 C24 -2.2(7) . . . . ?
O8 C22 C23 C24 177.4(4) . . . . ?
O7 C22 C23 C28 179.4(4) . . . . ?
O8 C22 C23 C28 -1.0(6) . . . . ?
C28 C23 C24 C25 0.1(6) . . . . ?
C22 C23 C24 C25 -178.4(4) . . . . ?
C23 C24 C25 C26 0.0(6) . . . . ?
C24 C25 C26 N4 177.9(4) . . . . ?
C24 C25 C26 C27 -0.8(6) . . . . ?
N4 C26 C27 C28 -177.1(4) . . . . ?
C25 C26 C27 C28 1.6(6) . . . . ?
C26 C27 C28 C23 -1.5(7) . . . . ?
C24 C23 C28 C27 0.7(6) . . . . ?
C22 C23 C28 C27 179.1(4) . . . . ?
O9 C29 C30 C31 -179.8(4) . . . . ?
O10 C29 C30 C31 -0.6(6) . . . . ?
O9 C29 C30 C35 -0.7(7) . . . . ?
O10 C29 C30 C35 178.6(4) . . . . ?
C35 C30 C31 C32 1.2(6) . . . . ?
C29 C30 C31 C32 -179.6(4) . . . . ?
C30 C31 C32 C33 0.1(6) . . . . ?
C31 C32 C33 N5 177.4(4) . . . . ?
C31 C32 C33 C34 -0.8(6) . . . . ?
N5 C33 C34 C35 -178.0(4) . . . . ?
C32 C33 C34 C35 0.3(6) . . . . ?
C33 C34 C35 C30 1.0(7) . . . . ?
C31 C30 C35 C34 -1.8(6) . . . . ?
C29 C30 C35 C34 179.0(4) . . . . ?
O11 C36 C37 C42 -0.8(7) . . . . ?
O12 C36 C37 C42 178.8(4) . . . . ?
O11 C36 C37 C38 179.9(4) . . . . ?
O12 C36 C37 C38 -0.5(7) . . . . ?
C42 C37 C38 C39 0.5(7) . . . . ?
C36 C37 C38 C39 179.8(4) . . . . ?
C37 C38 C39 C40 0.6(7) . . . . ?
C38 C39 C40 N6 177.9(4) . . . . ?
C38 C39 C40 C41 -0.7(7) . . . . ?
N6 C40 C41 C42 -178.8(4) . . . . ?
C39 C40 C41 C42 -0.1(7) . . . . ?
C40 C41 C42 C37 1.2(7) . . . . ?
C38 C37 C42 C41 -1.4(7) . . . . ?
C36 C37 C42 C41 179.3(4) . . . . ?
O14 C43 C44 O13 56.5(6) . . . . ?
O13 C45 C46 O14 -58.0(6) . . . . ?
O16 C47 C48 O15 -58.0(6) . . . . ?
O15 C49 C50 O16 59.1(6) . . . . ?
C46 C45 O13 C44 56.9(6) . . . . ?
C43 C44 O13 C45 -56.5(6) . . . . ?
C44 C43 O14 C46 -56.3(6) . . . . ?
C45 C46 O14 C43 57.4(6) . . . . ?
C47 C48 O15 C49 57.8(6) . . . . ?
C50 C49 O15 C48 -58.6(6) . . . . ?
C48 C47 O16 C50 57.9(6) . . . . ?
C49 C50 O16 C47 -58.4(6) . . . . ?
C52 C51 O17 C52 -56.9(5) 3_667 . . . ?
C51 C52 O17 C51 56.5(6) 3_667 . . . ?
C54 C53 O18 C54 55.3(6) 3_566 . . . ?
C53 C54 O18 C53 -55.5(6) 3_566 . . . ?
