#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:46:07 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246211.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_7246211
loop_
_publ_author_name
'Nandi, Sujay Kumar'
'Roy, Samrat'
'Pal, Bipul'
'Haldar, Debasish'
_publ_section_title
;
 Polarization-dependent second harmonic generation in peptide crystals:
 effects of molecular packing.
;
_journal_issue                   7
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              5849
_journal_page_last               5856
_journal_paper_doi               10.1039/d2cp05462k
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration s
_chemical_formula_moiety         'C20 H16 N2 O7'
_chemical_formula_sum            'C20 H16 N2 O7'
_chemical_formula_weight         396.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-05-26 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.22810(10)
_cell_length_b                   10.50560(10)
_cell_length_c                   21.3512(3)
_cell_measurement_reflns_used    7466
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.7230
_cell_measurement_theta_min      4.1280
_cell_volume                     1845.62(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6472   57.0000 -120.0000 115

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6472   57.0000    0.0000 115

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6472  -99.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236   61.0000  -90.0000 118

#__ type_ start__ end____ width___ exp.time_
  5 omega  100.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236  111.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236  178.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega   17.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236   45.0000    0.0000 131

#__ type_ start__ end____ width___ exp.time_
  8 omega  101.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
  9 omega   86.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
 10 omega  101.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  150.0000 77

#__ type_ start__ end____ width___ exp.time_
 11 omega   20.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
 12 omega   68.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000    0.0000 110

#__ type_ start__ end____ width___ exp.time_
 13 omega   70.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  -30.0000 108

#__ type_ start__ end____ width___ exp.time_
 14 omega  101.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
 15 omega   29.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -135.0000   -4.0000 97

#__ type_ start__ end____ width___ exp.time_
 16 omega  -13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6472   57.0000  120.0000 115

#__ type_ start__ end____ width___ exp.time_
 17 omega  -51.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6472  -57.0000 -120.0000 115

#__ type_ start__ end____ width___ exp.time_
 18 omega  -51.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6472  -57.0000    0.0000 115

#__ type_ start__ end____ width___ exp.time_
 19 omega   27.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236   61.0000 -150.0000 118

#__ type_ start__ end____ width___ exp.time_
 20 omega   27.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236   61.0000   60.0000 118

#__ type_ start__ end____ width___ exp.time_
 21 omega  100.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236  111.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 22 omega   17.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236   45.0000  150.0000 131

#__ type_ start__ end____ width___ exp.time_
 23 omega   20.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236   81.0000  -73.6989 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  100.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.8236  111.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 25 omega   20.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
 26 omega   56.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000  120.0000 122

#__ type_ start__ end____ width___ exp.time_
 27 omega   33.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000 -150.0000 145

#__ type_ start__ end____ width___ exp.time_
 28 omega   64.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 114

#__ type_ start__ end____ width___ exp.time_
 29 omega   64.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -71.6175 114

#__ type_ start__ end____ width___ exp.time_
 30 omega   56.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000  -90.0000 122

#__ type_ start__ end____ width___ exp.time_
 31 omega   64.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0166042000
_diffrn_orient_matrix_UB_12      -0.1271665000
_diffrn_orient_matrix_UB_13      0.0353511000
_diffrn_orient_matrix_UB_21      0.0226850000
_diffrn_orient_matrix_UB_22      -0.0730252000
_diffrn_orient_matrix_UB_23      -0.0619977000
_diffrn_orient_matrix_UB_31      0.1850293000
_diffrn_orient_matrix_UB_32      -0.0024694000
_diffrn_orient_matrix_UB_33      0.0107498000
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14811
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        65.815
_diffrn_reflns_theta_max         65.815
_diffrn_reflns_theta_min         4.141
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2547
_exptl_crystal_size_mid          0.2248
_exptl_crystal_size_min          0.1958
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0385
_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)+(0.0473P)²+0.2294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2981
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cp05462k2.cif
_cod_data_source_block           couphe
_cod_depositor_comments
'Adding full bibliography for 7246211--7246213.cif.'
_cod_database_code               7246211
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_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.
;
_reflns_odcompleteness_completeness 97.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C5(H5), C2(H2A), C3(H3), C18(H18), C14(H14), C17(H17),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_date_sample_data_collection 2018-12-02
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O3 O 0.5546(3) 0.57105(17) 0.66525(10) 0.0532(5) Uani 1 1 d . . . . .
O5 O 0.9470(3) 0.25229(19) 0.61109(10) 0.0560(5) Uani 1 1 d . . . . .
O4 O 0.7803(3) 0.6319(2) 0.62021(12) 0.0648(6) Uani 1 1 d . . . . .
O7 O 1.3907(3) 0.5338(2) 0.52228(11) 0.0673(6) Uani 1 1 d . . . . .
O2 O 0.1407(3) 0.0980(2) 0.74026(12) 0.0701(7) Uani 1 1 d . . . . .
N2 N 1.0001(3) 0.4545(2) 0.58266(10) 0.0467(5) Uani 1 1 d . . . . .
H2 H 0.9672 0.5322 0.5839 0.056 Uiso 1 1 calc R U . . .
O6 O 1.1846(3) 0.6527(2) 0.55638(12) 0.0706(6) Uani 1 1 d . . . . .
N1 N 0.1056(3) 0.2110(3) 0.74395(11) 0.0576(6) Uani 1 1 d . . . . .
O1 O -0.0253(3) 0.2501(3) 0.76266(13) 0.0835(8) Uani 1 1 d . . . . .
C10 C 0.9087(3) 0.3649(3) 0.60923(12) 0.0429(6) Uani 1 1 d . . . . .
C6 C 0.4904(3) 0.3515(3) 0.68330(11) 0.0423(6) Uani 1 1 d . . . . .
C19 C 1.2431(4) 0.5517(3) 0.54442(13) 0.0502(7) Uani 1 1 d . . . . .
C8 C 0.7493(3) 0.4081(3) 0.63665(12) 0.0416(6) Uani 1 1 d . . . . .
C1 C 0.4489(4) 0.4799(3) 0.68584(12) 0.0451(6) Uani 1 1 d . . . . .
C7 C 0.6471(3) 0.3189(2) 0.65865(11) 0.0414(6) Uani 1 1 d . . . . .
H7 H 0.6788 0.2339 0.6579 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7030(4) 0.5422(3) 0.63848(12) 0.0473(6) Uani 1 1 d . . . . .
C4 C 0.2279(4) 0.3047(3) 0.72461(12) 0.0495(7) Uani 1 1 d . . . . .
C5 C 0.3758(4) 0.2615(3) 0.70296(12) 0.0449(6) Uani 1 1 d . . . . .
H5 H 0.3989 0.1749 0.7015 0.054 Uiso 1 1 calc R U . . .
C11 C 1.1533(4) 0.4262(3) 0.55164(12) 0.0473(7) Uani 1 1 d . . . . .
H11 H 1.2173 0.3702 0.5788 0.057 Uiso 1 1 calc R U . . .
C12 C 1.1289(4) 0.3594(3) 0.48778(13) 0.0516(7) Uani 1 1 d . . . . .
H12A H 1.2345 0.3434 0.4692 0.062 Uiso 1 1 calc R U . . .
H12B H 1.0770 0.2777 0.4948 0.062 Uiso 1 1 calc R U . . .
C13 C 1.0273(4) 0.4353(3) 0.44226(12) 0.0483(6) Uani 1 1 d . . . . .
C2 C 0.3012(4) 0.5216(3) 0.70851(14) 0.0552(7) Uani 1 1 d . . . . .
H2A H 0.2777 0.6081 0.7106 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1894(4) 0.4327(3) 0.72788(14) 0.0565(7) Uani 1 1 d . . . . .
H3 H 0.0887 0.4585 0.7431 0.068 Uiso 1 1 calc R U . . .
C18 C 1.0986(5) 0.5230(3) 0.40231(13) 0.0616(8) Uani 1 1 d . . . . .
H18 H 1.2107 0.5346 0.4025 0.074 Uiso 1 1 calc R U . . .
C14 C 0.8611(4) 0.4197(3) 0.43970(14) 0.0606(8) Uani 1 1 d . . . . .
H14 H 0.8116 0.3608 0.4661 0.073 Uiso 1 1 calc R U . . .
C17 C 1.0010(6) 0.5939(3) 0.36171(15) 0.0764(12) Uani 1 1 d . . . . .
H17 H 1.0488 0.6536 0.3353 0.092 Uiso 1 1 calc R U . . .
C15 C 0.7663(5) 0.4897(4) 0.39878(17) 0.0750(10) Uani 1 1 d . . . . .
H15 H 0.6544 0.4772 0.3976 0.090 Uiso 1 1 calc R U . . .
C16 C 0.8372(6) 0.5770(4) 0.36021(17) 0.0800(12) Uani 1 1 d . . . . .
H16 H 0.7737 0.6249 0.3330 0.096 Uiso 1 1 calc R U . . .
C20 C 1.4783(5) 0.6502(4) 0.5064(2) 0.0784(11) Uani 1 1 d . . . . .
H20A H 1.4247 0.6920 0.4721 0.118 Uiso 1 1 calc R U . . .
H20B H 1.5877 0.6294 0.4945 0.118 Uiso 1 1 calc R U . . .
H20C H 1.4801 0.7058 0.5421 0.118 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
C1 O3 C9 122.8(2) . . ?
C19 O7 C20 114.7(3) . . ?
C10 N2 H2 118.7 . . ?
C10 N2 C11 122.6(2) . . ?
C11 N2 H2 118.7 . . ?
O2 N1 C4 118.1(3) . . ?
O1 N1 O2 123.8(3) . . ?
O1 N1 C4 118.2(3) . . ?
O5 C10 N2 123.5(3) . . ?
O5 C10 C8 120.1(2) . . ?
N2 C10 C8 116.4(2) . . ?
C1 C6 C7 117.8(2) . . ?
C1 C6 C5 118.5(3) . . ?
C5 C6 C7 123.7(2) . . ?
O7 C19 C11 111.1(3) . . ?
O6 C19 O7 125.2(3) . . ?
O6 C19 C11 123.6(3) . . ?
C7 C8 C10 118.1(2) . . ?
C7 C8 C9 120.0(3) . . ?
C9 C8 C10 121.9(2) . . ?
O3 C1 C6 120.7(3) . . ?
O3 C1 C2 116.8(2) . . ?
C2 C1 C6 122.5(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
O3 C9 C8 117.0(2) . . ?
O4 C9 O3 115.5(3) . . ?
O4 C9 C8 127.6(3) . . ?
C5 C4 N1 118.6(3) . . ?
C5 C4 C3 122.6(3) . . ?
C3 C4 N1 118.7(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
N2 C11 C19 106.9(2) . . ?
N2 C11 H11 108.6 . . ?
N2 C11 C12 112.4(2) . . ?
C19 C11 H11 108.6 . . ?
C19 C11 C12 111.6(2) . . ?
C12 C11 H11 108.6 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C11 113.5(2) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C18 C13 C12 120.9(3) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 C18 118.4(3) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2A 120.7 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C13 C18 H18 120.2 . . ?
C13 C18 C17 119.5(4) . . ?
C17 C18 H18 120.2 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O3 C1 1.366(3) . ?
O3 C9 1.382(4) . ?
O5 C10 1.225(3) . ?
O4 C9 1.202(3) . ?
O7 C19 1.317(4) . ?
O7 C20 1.460(4) . ?
O2 N1 1.225(4) . ?
N2 H2 0.8600 . ?
N2 C10 1.331(4) . ?
N2 C11 1.455(4) . ?
O6 C19 1.192(4) . ?
N1 O1 1.220(4) . ?
N1 C4 1.467(4) . ?
C10 C8 1.506(4) . ?
C6 C1 1.392(4) . ?
C6 C7 1.435(4) . ?
C6 C5 1.399(4) . ?
C19 C11 1.520(4) . ?
C8 C7 1.344(4) . ?
C8 C9 1.460(4) . ?
C1 C2 1.380(4) . ?
C7 H7 0.9300 . ?
C4 C5 1.379(4) . ?
C4 C3 1.384(4) . ?
C5 H5 0.9300 . ?
C11 H11 0.9800 . ?
C11 C12 1.547(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.510(4) . ?
C13 C18 1.386(4) . ?
C13 C14 1.379(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.397(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.360(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(6) . ?
C16 H16 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O3 C1 C2 C3 178.0(3) . . . . ?
O5 C10 C8 C7 -4.8(4) . . . . ?
O5 C10 C8 C9 176.6(3) . . . . ?
O7 C19 C11 N2 173.8(2) . . . . ?
O7 C19 C11 C12 -62.9(3) . . . . ?
O2 N1 C4 C5 0.3(4) . . . . ?
O2 N1 C4 C3 179.3(3) . . . . ?
N2 C10 C8 C7 173.9(2) . . . . ?
N2 C10 C8 C9 -4.7(3) . . . . ?
N2 C11 C12 C13 58.2(3) . . . . ?
O6 C19 C11 N2 -7.5(4) . . . . ?
O6 C19 C11 C12 115.8(3) . . . . ?
N1 C4 C5 C6 178.6(2) . . . . ?
N1 C4 C3 C2 -178.4(3) . . . . ?
O1 N1 C4 C5 -179.5(3) . . . . ?
O1 N1 C4 C3 -0.5(4) . . . . ?
C10 N2 C11 C19 -164.0(2) . . . . ?
C10 N2 C11 C12 73.3(3) . . . . ?
C10 C8 C7 C6 -177.6(2) . . . . ?
C10 C8 C9 O3 -179.4(2) . . . . ?
C10 C8 C9 O4 -0.7(4) . . . . ?
C6 C1 C2 C3 -1.6(4) . . . . ?
C19 C11 C12 C13 -61.9(3) . . . . ?
C1 O3 C9 O4 177.0(3) . . . . ?
C1 O3 C9 C8 -4.1(4) . . . . ?
C1 C6 C7 C8 -2.2(4) . . . . ?
C1 C6 C5 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C7 C6 C1 O3 0.2(4) . . . . ?
C7 C6 C1 C2 179.8(3) . . . . ?
C7 C6 C5 C4 -178.7(2) . . . . ?
C7 C8 C9 O3 2.0(4) . . . . ?
C7 C8 C9 O4 -179.3(3) . . . . ?
C9 O3 C1 C6 3.1(4) . . . . ?
C9 O3 C1 C2 -176.6(3) . . . . ?
C9 C8 C7 C6 1.1(4) . . . . ?
C5 C6 C1 O3 -177.8(2) . . . . ?
C5 C6 C1 C2 1.8(4) . . . . ?
C5 C6 C7 C8 175.7(2) . . . . ?
C5 C4 C3 C2 0.5(5) . . . . ?
C11 N2 C10 O5 1.7(4) . . . . ?
C11 N2 C10 C8 -177.0(2) . . . . ?
C11 C12 C13 C18 88.6(3) . . . . ?
C11 C12 C13 C14 -91.0(3) . . . . ?
C12 C13 C18 C17 -178.5(3) . . . . ?
C12 C13 C14 C15 179.2(3) . . . . ?
C13 C18 C17 C16 -0.8(5) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C18 C13 C14 C15 -0.4(5) . . . . ?
C18 C17 C16 C15 0.0(6) . . . . ?
C14 C13 C18 C17 1.0(4) . . . . ?
C14 C15 C16 C17 0.7(6) . . . . ?
C20 O7 C19 O6 -6.1(5) . . . . ?
C20 O7 C19 C11 172.6(3) . . . . ?
