#------------------------------------------------------------------------------
#$Date: 2023-07-21 04:15:44 +0300 (Fri, 21 Jul 2023) $
#$Revision: 285306 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/70/7247087.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_7247087
loop_
_publ_author_name
'Liu, Xiaoting'
'Cui, Jingliang'
'Zeng, Qun'
'Fang, Liwen'
'Liang, Peng-Yu'
'Zhou, Pan-Pan'
'Parkin, Sean'
'Li, Tonglei'
'Ruan, Shigang'
'Long, Sihui'
_publ_section_title
;
 Solvatomorphism and first-time observation of acid--acid catemer in
 4-phenylamino-benzoic acids
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              21021
_journal_page_last               21035
_journal_paper_doi               10.1039/D3RA04102F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.8907(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8309(2)
_cell_length_b                   16.98433(19)
_cell_length_c                   11.30860(15)
_cell_measurement_reflns_used    13270
_cell_measurement_temperature    287.3(3)
_cell_measurement_theta_max      75.9220
_cell_measurement_theta_min      2.6080
_cell_volume                     2876.85(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      287.3(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  75.00   0.50    0.05    --   47.57  54.00  91.00   52
  2  ω     83.00 111.00   0.50    0.05    --   47.57  54.00  91.00   56
  3  ω     97.00 175.00   0.50    0.07    --  107.75  54.00  91.00  156
  4  ω    150.00 175.00   0.50    0.07    --  107.75  19.00  30.00   50
  5  ω    102.00 127.00   0.50    0.07    --  107.75  19.00  30.00   50
  6  ω     98.00 170.00   0.50    0.07    --  107.75  37.00-150.00  144
  7  ω     51.00  92.00   0.50    0.07    --  107.75 -77.00 -30.00   82
  8  ω     37.00  63.00   0.50    0.07    --  107.75 -57.00 -60.00   52
  9  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00-120.00   50
 10  ω    -24.00  49.00   0.50    0.05    --   47.57 -54.00 -52.00  146
 11  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00 150.00   50
 12  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00  90.00   50
 13  ω     37.00  86.00   0.50    0.07    --  107.75 -77.00-120.00   98
 14  ω    -25.00  23.00   0.50    0.05    --   47.57 -19.00-120.00   96
 15  ω    -94.00 -24.00   0.50    0.05    --  -47.57 125.00-150.00  140
 16  ω   -126.00 -88.00   0.50    0.07    -- -100.00 -19.00   0.00   76
 17  ω   -137.00-111.00   0.50    0.07    -- -100.00 -54.00 -52.00   52
 18  ω   -175.00-147.00   0.50    0.07    -- -100.00 -19.00   0.00   56
 19  ω   -166.00-124.00   0.50    0.07    -- -100.00 -57.00  30.00   84
 20  ω   -110.00 -85.00   0.50    0.07    -- -100.00 -57.00  30.00   50
 21  ω    -82.00 -56.00   0.50    0.05    --  -47.57 -54.00 -52.00   52
 22  ω    -65.00 -27.00   0.50    0.07    -- -100.00  54.00  91.00   76
 23  ω    -69.00 -28.00   0.50    0.07    -- -100.00  57.00 120.00   82
 24  ω   -109.00 -73.00   0.50    0.07    -- -100.00  77.00 -90.00   72
 25  ω    -68.00 -30.00   0.50    0.07    -- -100.00  77.00 -90.00   76
 26  ω    -65.00 -40.00   0.50    0.07    -- -100.00  57.00-120.00   50
 27  ω    -68.00 -31.00   0.50    0.07    -- -100.00  57.00 -90.00   74
 28  ω    -68.00 -33.00   0.50    0.07    -- -100.00  57.00 -60.00   70
 29  ω    -62.00  24.00   0.50    0.05    --  -47.57  54.00  91.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0764030000
_diffrn_orient_matrix_UB_12      -0.0554612000
_diffrn_orient_matrix_UB_13      -0.0026149000
_diffrn_orient_matrix_UB_21      -0.0504495000
_diffrn_orient_matrix_UB_22      -0.0198085000
_diffrn_orient_matrix_UB_23      -0.1377403000
_diffrn_orient_matrix_UB_31      0.0468505000
_diffrn_orient_matrix_UB_32      0.0689982000
_diffrn_orient_matrix_UB_33      -0.0418017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22319
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.506
_diffrn_reflns_theta_min         2.950
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0079(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0501
_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)+(0.0926P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4782
_reflns_number_total             5795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra04102f2.cif
_cod_data_source_block           8-I
_cod_database_code               7247087
_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_max   0.958
_shelx_estimated_absorpt_t_min   0.918
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12), N2(H2A),
 C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C28(H28)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.585
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
O1 O 0.18860(10) 0.52817(7) 0.61310(11) 0.0903(4) Uani 1 1 d . . . . .
H1 H 0.2129 0.4869 0.6437 0.135 Uiso 1 1 calc R U . . .
O2 O 0.25045(8) 0.56782(6) 0.81022(11) 0.0843(3) Uani 1 1 d . . . . .
N1 N 0.03897(9) 0.87620(8) 0.56106(11) 0.0796(4) Uani 1 1 d . . . . .
H1A H 0.0003 0.8805 0.4877 0.096 Uiso 1 1 calc R U . . .
C1 C 0.07984(10) 0.80498(8) 0.59554(13) 0.0648(3) Uani 1 1 d . . . . .
C2 C 0.13023(10) 0.78852(8) 0.71899(13) 0.0682(4) Uani 1 1 d . . . . .
H2 H 0.1374 0.8271 0.7798 0.082 Uiso 1 1 calc R U . . .
C3 C 0.16944(10) 0.71599(8) 0.75208(13) 0.0674(4) Uani 1 1 d . . . . .
H3 H 0.2024 0.7061 0.8351 0.081 Uiso 1 1 calc R U . . .
C4 C 0.16038(9) 0.65739(8) 0.66314(13) 0.0629(3) Uani 1 1 d . . . . .
C5 C 0.11001(12) 0.67364(9) 0.53960(14) 0.0743(4) Uani 1 1 d . . . . .
H5 H 0.1029 0.6350 0.4789 0.089 Uiso 1 1 calc R U . . .
C6 C 0.07088(12) 0.74578(9) 0.50624(13) 0.0758(4) Uani 1 1 d . . . . .
H6 H 0.0379 0.7555 0.4232 0.091 Uiso 1 1 calc R U . . .
C7 C 0.20268(10) 0.58037(8) 0.69808(13) 0.0654(3) Uani 1 1 d . . . . .
C8 C 0.05696(10) 0.94380(8) 0.64018(12) 0.0667(4) Uani 1 1 d . . . . .
C9 C 0.12147(10) 0.99762(9) 0.63209(13) 0.0706(4) Uani 1 1 d . . . . .
C10 C 0.13500(11) 1.06432(10) 0.70594(16) 0.0790(4) Uani 1 1 d . . . . .
H10 H 0.1765 1.1013 0.6993 0.095 Uiso 1 1 calc R U . . .
C11 C 0.08917(12) 1.07825(10) 0.78951(16) 0.0816(5) Uani 1 1 d . . . . .
C12 C 0.02759(12) 1.02257(11) 0.79708(16) 0.0828(5) Uani 1 1 d . . . . .
H12 H -0.0030 1.0304 0.8539 0.099 Uiso 1 1 calc R U . . .
C13 C 0.00956(10) 0.95556(9) 0.72343(15) 0.0742(4) Uani 1 1 d . . . . .
C14 C 0.17573(13) 0.98330(13) 0.54726(17) 0.0957(6) Uani 1 1 d . . . . .
H14A H 0.2129 0.9379 0.5755 0.143 Uiso 1 1 calc R U . . .
H14B H 0.2125 1.0284 0.5483 0.143 Uiso 1 1 calc R U . . .
H14C H 0.1365 0.9745 0.4637 0.143 Uiso 1 1 calc R U . . .
C15 C 0.10711(18) 1.15070(14) 0.8704(2) 0.1242(8) Uani 1 1 d . . . . .
H15A H 0.0611 1.1889 0.8354 0.186 Uiso 1 1 calc R U . . .
H15B H 0.1639 1.1725 0.8744 0.186 Uiso 1 1 calc R U . . .
H15C H 0.1078 1.1369 0.9530 0.186 Uiso 1 1 calc R U . . .
C16 C -0.05998(13) 0.89721(12) 0.7327(2) 0.0981(6) Uani 1 1 d . . . . .
H16A H -0.1070 0.8943 0.6538 0.147 Uiso 1 1 calc R U . . .
H16B H -0.0841 0.9140 0.7962 0.147 Uiso 1 1 calc R U . . .
H16C H -0.0330 0.8463 0.7538 0.147 Uiso 1 1 calc R U . . .
O3 O 0.31592(9) 0.42478(6) 0.87210(11) 0.0833(3) Uani 1 1 d . . . . .
H3A H 0.2971 0.4680 0.8428 0.125 Uiso 1 1 calc R U . . .
O4 O 0.26827(10) 0.39349(7) 0.66993(11) 0.0956(4) Uani 1 1 d . . . . .
N2 N 0.43262(10) 0.06587(8) 0.90535(11) 0.0805(4) Uani 1 1 d . . . . .
H2A H 0.4652 0.0590 0.9819 0.097 Uiso 1 1 calc R U . . .
C17 C 0.30558(10) 0.37548(9) 0.78363(14) 0.0685(4) Uani 1 1 d . . . . .
C18 C 0.33745(9) 0.29478(8) 0.81460(13) 0.0636(3) Uani 1 1 d . . . . .
C19 C 0.38250(11) 0.27252(9) 0.93785(14) 0.0729(4) Uani 1 1 d . . . . .
H19 H 0.3923 0.3096 1.0014 0.087 Uiso 1 1 calc R U . . .
C20 C 0.41238(11) 0.19734(10) 0.96651(13) 0.0747(4) Uani 1 1 d . . . . .
H20 H 0.4415 0.1837 1.0494 0.090 Uiso 1 1 calc R U . . .
C21 C 0.39971(9) 0.14053(8) 0.87262(13) 0.0639(3) Uani 1 1 d . . . . .
C22 C 0.35402(9) 0.16198(8) 0.74939(13) 0.0636(3) Uani 1 1 d . . . . .
H22 H 0.3440 0.1249 0.6859 0.076 Uiso 1 1 calc R U . . .
C23 C 0.32367(9) 0.23804(8) 0.72141(12) 0.0640(3) Uani 1 1 d . . . . .
H23 H 0.2935 0.2517 0.6388 0.077 Uiso 1 1 calc R U . . .
C24 C 0.41851(10) -0.00124(9) 0.82607(13) 0.0687(4) Uani 1 1 d . . . . .
C25 C 0.36574(10) -0.06297(10) 0.84538(15) 0.0777(4) Uani 1 1 d . . . . .
C26 C 0.35815(12) -0.13049(11) 0.77469(19) 0.0902(5) Uani 1 1 d . . . . .
H26 H 0.3249 -0.1723 0.7893 0.108 Uiso 1 1 calc R U . . .
C27 C 0.39787(13) -0.13845(11) 0.6833(2) 0.0927(5) Uani 1 1 d . . . . .
C28 C 0.44834(12) -0.07617(11) 0.66530(17) 0.0873(5) Uani 1 1 d . . . . .
H28 H 0.4750 -0.0803 0.6034 0.105 Uiso 1 1 calc R U . . .
C29 C 0.46104(11) -0.00765(9) 0.73550(14) 0.0744(4) Uani 1 1 d . . . . .
C30 C 0.31706(14) -0.05600(15) 0.93962(19) 0.1046(6) Uani 1 1 d . . . . .
H30A H 0.3596 -0.0541 1.0223 0.157 Uiso 1 1 calc R U . . .
H30B H 0.2787 -0.1007 0.9325 0.157 Uiso 1 1 calc R U . . .
H30C H 0.2820 -0.0087 0.9240 0.157 Uiso 1 1 calc R U . . .
C31 C 0.38545(19) -0.21176(16) 0.6034(3) 0.1442(10) Uani 1 1 d . . . . .
H31A H 0.3811 -0.1973 0.5196 0.216 Uiso 1 1 calc R U . . .
H31B H 0.3318 -0.2383 0.6029 0.216 Uiso 1 1 calc R U . . .
H31C H 0.4356 -0.2462 0.6371 0.216 Uiso 1 1 calc R U . . .
C32 C 0.52052(14) 0.05633(12) 0.71407(19) 0.0948(5) Uani 1 1 d . . . . .
H32A H 0.4886 0.0858 0.6408 0.142 Uiso 1 1 calc R U . . .
H32B H 0.5726 0.0331 0.7027 0.142 Uiso 1 1 calc R U . . .
H32C H 0.5382 0.0908 0.7851 0.142 Uiso 1 1 calc R U . . .
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
C7 O1 H1 109.5 . . ?
C1 N1 H1A 118.2 . . ?
C1 N1 C8 123.58(11) . . ?
C8 N1 H1A 118.2 . . ?
N1 C1 C2 121.84(13) . . ?
N1 C1 C6 120.11(12) . . ?
C2 C1 C6 118.04(13) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.91(13) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.86(13) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.38(13) . . ?
C3 C4 C7 120.91(13) . . ?
C5 C4 C7 120.71(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.95(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.86(13) . . ?
C5 C6 H6 119.6 . . ?
O1 C7 C4 117.74(13) . . ?
O2 C7 O1 122.72(13) . . ?
O2 C7 C4 119.54(13) . . ?
C9 C8 N1 119.20(14) . . ?
C13 C8 N1 119.78(15) . . ?
C13 C8 C9 121.02(14) . . ?
C8 C9 C14 121.22(15) . . ?
C10 C9 C8 118.08(15) . . ?
C10 C9 C14 120.69(16) . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.63(16) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C15 121.1(2) . . ?
C12 C11 C10 117.48(16) . . ?
C12 C11 C15 121.38(19) . . ?
C11 C12 H12 118.7 . . ?
C11 C12 C13 122.56(16) . . ?
C13 C12 H12 118.7 . . ?
C8 C13 C16 121.08(16) . . ?
C12 C13 C8 118.19(16) . . ?
C12 C13 C16 120.73(16) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 O3 H3A 109.5 . . ?
C21 N2 H2A 116.5 . . ?
C21 N2 C24 126.92(12) . . ?
C24 N2 H2A 116.5 . . ?
O3 C17 C18 118.75(13) . . ?
O4 C17 O3 122.52(14) . . ?
O4 C17 C18 118.72(13) . . ?
C19 C18 C17 121.16(13) . . ?
C23 C18 C17 120.65(13) . . ?
C23 C18 C19 118.19(13) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.09(14) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.76(13) . . ?
C21 C20 H20 119.6 . . ?
N2 C21 C20 118.85(12) . . ?
N2 C21 C22 122.58(13) . . ?
C22 C21 C20 118.57(13) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.23(13) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.15(12) . . ?
C22 C23 H23 119.4 . . ?
C25 C24 N2 118.77(14) . . ?
C29 C24 N2 120.58(15) . . ?
C29 C24 C25 120.53(15) . . ?
C24 C25 C30 121.21(17) . . ?
C26 C25 C24 118.41(16) . . ?
C26 C25 C30 120.37(18) . . ?
C25 C26 H26 118.7 . . ?
C27 C26 C25 122.67(18) . . ?
C27 C26 H26 118.7 . . ?
C26 C27 C28 117.51(18) . . ?
C26 C27 C31 121.7(2) . . ?
C28 C27 C31 120.8(2) . . ?
C27 C28 H28 118.6 . . ?
C27 C28 C29 122.85(17) . . ?
C29 C28 H28 118.6 . . ?
C24 C29 C32 122.33(16) . . ?
C28 C29 C24 117.98(16) . . ?
C28 C29 C32 119.68(16) . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
O1 H1 0.8200 . ?
O1 C7 1.2730(18) . ?
O2 C7 1.2667(18) . ?
N1 H1A 0.8600 . ?
N1 C1 1.3677(18) . ?
N1 C8 1.4264(19) . ?
C1 C2 1.3937(19) . ?
C1 C6 1.399(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3757(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C4 C5 1.394(2) . ?
C4 C7 1.4644(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.396(2) . ?
C8 C13 1.395(2) . ?
C9 C10 1.382(2) . ?
C9 C14 1.500(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 C12 1.381(3) . ?
C11 C15 1.504(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(2) . ?
C13 C16 1.510(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O3 H3A 0.8200 . ?
O3 C17 1.2740(18) . ?
O4 C17 1.2665(18) . ?
N2 H2A 0.8600 . ?
N2 C21 1.3754(18) . ?
N2 C24 1.422(2) . ?
C17 C18 1.463(2) . ?
C18 C19 1.397(2) . ?
C18 C23 1.3922(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.400(2) . ?
C21 C22 1.3947(19) . ?
C22 H22 0.9300 . ?
C22 C23 1.3788(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.401(2) . ?
C24 C29 1.400(2) . ?
C25 C26 1.381(3) . ?
C25 C30 1.508(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.379(3) . ?
C27 C28 1.380(3) . ?
C27 C31 1.513(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.386(2) . ?
C29 C32 1.508(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
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
N1 C1 C2 C3 178.79(15) . . . . ?
N1 C1 C6 C5 -178.79(16) . . . . ?
N1 C8 C9 C10 177.31(12) . . . . ?
N1 C8 C9 C14 -3.56(19) . . . . ?
N1 C8 C13 C12 -178.80(12) . . . . ?
N1 C8 C13 C16 0.8(2) . . . . ?
C1 N1 C8 C9 93.11(18) . . . . ?
C1 N1 C8 C13 -87.45(19) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C7 179.51(14) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C7 O1 177.04(14) . . . . ?
C3 C4 C7 O2 -2.2(2) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C5 C4 C7 O1 -3.0(2) . . . . ?
C5 C4 C7 O2 177.79(14) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C7 C4 C5 C6 -179.50(15) . . . . ?
C8 N1 C1 C2 12.2(2) . . . . ?
C8 N1 C1 C6 -168.61(15) . . . . ?
C8 C9 C10 C11 2.0(2) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
C9 C8 C13 C16 -179.74(13) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C9 C10 C11 C15 178.66(16) . . . . ?
C10 C11 C12 C13 -1.3(2) . . . . ?
C11 C12 C13 C8 1.1(2) . . . . ?
C11 C12 C13 C16 -178.50(15) . . . . ?
C13 C8 C9 C10 -2.13(19) . . . . ?
C13 C8 C9 C14 177.01(13) . . . . ?
C14 C9 C10 C11 -177.15(15) . . . . ?
C15 C11 C12 C13 179.74(16) . . . . ?
O3 C17 C18 C19 -3.2(2) . . . . ?
O3 C17 C18 C23 176.88(14) . . . . ?
O4 C17 C18 C19 177.21(15) . . . . ?
O4 C17 C18 C23 -2.7(2) . . . . ?
N2 C21 C22 C23 -178.93(14) . . . . ?
N2 C24 C25 C26 -174.94(13) . . . . ?
N2 C24 C25 C30 5.9(2) . . . . ?
N2 C24 C29 C28 176.77(13) . . . . ?
N2 C24 C29 C32 -2.2(2) . . . . ?
C17 C18 C19 C20 -179.81(15) . . . . ?
C17 C18 C23 C22 179.49(13) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C19 C18 C23 C22 -0.4(2) . . . . ?
C19 C20 C21 N2 178.60(15) . . . . ?
C19 C20 C21 C22 -1.5(2) . . . . ?
C20 C21 C22 C23 1.1(2) . . . . ?
C21 N2 C24 C25 -110.87(17) . . . . ?
C21 N2 C24 C29 73.0(2) . . . . ?
C21 C22 C23 C18 -0.2(2) . . . . ?
C23 C18 C19 C20 0.1(2) . . . . ?
C24 N2 C21 C20 172.98(15) . . . . ?
C24 N2 C21 C22 -7.0(2) . . . . ?
C24 C25 C26 C27 -2.2(2) . . . . ?
C25 C24 C29 C28 0.8(2) . . . . ?
C25 C24 C29 C32 -178.23(14) . . . . ?
C25 C26 C27 C28 1.3(3) . . . . ?
C25 C26 C27 C31 -177.45(19) . . . . ?
C26 C27 C28 C29 0.8(3) . . . . ?
C27 C28 C29 C24 -1.7(2) . . . . ?
C27 C28 C29 C32 177.26(16) . . . . ?
C29 C24 C25 C26 1.1(2) . . . . ?
C29 C24 C25 C30 -178.00(14) . . . . ?
C30 C25 C26 C27 176.93(16) . . . . ?
C31 C27 C28 C29 179.51(19) . . . . ?
