#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223688.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223688
loop_
_publ_author_name
'Ravichandran, K.'
'Ramesh, P.'
'Sethuvasan, S.'
'Ponnuswamy, S.'
'Ponnuswamy, M. N.'
_publ_section_title
t-3-Ethyl-r-2,c-7-bis(4-methoxyphenyl)-1,4-diazepan-5-one
_journal_coeditor_code           CI2933
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2885
_journal_page_last               o2886
_journal_paper_doi               10.1107/S1600536809043311
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H26 N2 O3'
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_chemical_name_systematic
t-3-Ethyl-r-2,c-7-bis(4-methoxyphenyl)-1,4-diazepan-5-one
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.118(2)
_cell_angle_beta                 93.662(2)
_cell_angle_gamma                110.287(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5190(3)
_cell_length_b                   13.3480(4)
_cell_length_c                   15.0472(4)
_cell_measurement_reflns_used    4523
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.18
_cell_measurement_theta_min      1.40
_cell_volume                     1915.89(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46036
_diffrn_reflns_theta_full        29.18
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         10328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.06P)²+0.383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                6341
_reflns_number_total             10328
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2933.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1915.89(9)
_cod_database_code               2223688
_cod_database_fobs_code          2223688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A -0.01838(15) 0.04649(10) 0.27923(10) 0.0830(4) Uani d . 1 . .
O O2A 0.37857(13) -0.20475(10) -0.10577(10) 0.0756(4) Uani d . 1 . .
O O3A 0.69336(15) 0.71516(11) 0.19087(10) 0.0811(4) Uani d . 1 . .
N N1A 0.09646(14) 0.22089(11) 0.27464(10) 0.0560(3) Uani d . 1 . .
H H1A 0.0770(18) 0.2418(15) 0.3299(13) 0.066(5) Uiso d . 1 . .
N N5A 0.31252(13) 0.21527(10) 0.14281(8) 0.0475(3) Uani d . 1 . .
H H5A 0.3987(18) 0.2259(14) 0.1300(12) 0.060(5) Uiso d . 1 . .
C C2A 0.05133(16) 0.11262(14) 0.23888(12) 0.0573(4) Uani d . 1 . .
C C3A 0.09336(15) 0.07227(13) 0.14921(12) 0.0549(4) Uani d . 1 . .
H H3A 0.0620 0.1029 0.1031 0.066 Uiso calc R 1 . .
H H3B 0.0490 -0.0073 0.1296 0.066 Uiso calc R 1 . .
C C4A 0.24839(15) 0.10354(12) 0.15489(10) 0.0462(3) Uani d . 1 . .
H H4A 0.2850 0.1020 0.2159 0.055 Uiso calc R 1 . .
C C6A 0.32146(15) 0.30438(12) 0.22233(10) 0.0475(3) Uani d . 1 . .
H H6A 0.3576 0.2896 0.2778 0.057 Uiso calc R 1 . .
C C7A 0.17771(16) 0.30792(13) 0.23321(11) 0.0515(4) Uani d . 1 . .
H H7A 0.1292 0.2966 0.1720 0.062 Uiso calc R 1 . .
C C8A 0.28292(14) 0.02316(12) 0.08376(10) 0.0443(3) Uani d . 1 . .
C C9A 0.35352(16) -0.03896(13) 0.10915(12) 0.0533(4) Uani d . 1 . .
H H9A 0.3810 -0.0303 0.1712 0.064 Uiso calc R 1 . .
C C10A 0.38390(17) -0.11330(14) 0.04443(13) 0.0595(4) Uani d . 1 . .
H H10A 0.4327 -0.1534 0.0630 0.071 Uiso calc R 1 . .
C C11A 0.34280(15) -0.12864(13) -0.04710(12) 0.0546(4) Uani d . 1 . .
C C12A 0.27102(17) -0.06915(15) -0.07426(12) 0.0604(4) Uani d . 1 . .
H H12A 0.2418 -0.0795 -0.1363 0.072 Uiso calc R 1 . .
C C13A 0.24249(17) 0.00635(14) -0.00872(11) 0.0553(4) Uani d . 1 . .
H H13A 0.1946 0.0470 -0.0276 0.066 Uiso calc R 1 . .
C C14A 0.3381(3) -0.2238(2) -0.20034(18) 0.1147(10) Uani d . 1 . .
H H14A 0.3690 -0.2786 -0.2335 0.172 Uiso calc R 1 . .
H H14B 0.3775 -0.1565 -0.2191 0.172 Uiso calc R 1 . .
H H14C 0.2399 -0.2494 -0.2132 0.172 Uiso calc R 1 . .
C C15A 0.42113(16) 0.41145(12) 0.20960(10) 0.0486(3) Uani d . 1 . .
C C16A 0.40863(19) 0.44723(14) 0.13156(12) 0.0626(4) Uani d . 1 . .
H H16A 0.3384 0.4028 0.0837 0.075 Uiso calc R 1 . .
C C17A 0.4976(2) 0.54759(15) 0.12202(13) 0.0652(5) Uani d . 1 . .
H H17A 0.4867 0.5698 0.0684 0.078 Uiso calc R 1 . .
C C18A 0.60159(18) 0.61386(13) 0.19175(12) 0.0584(4) Uani d . 1 . .
C C19A 0.6171(2) 0.57884(16) 0.26968(14) 0.0773(6) Uani d . 1 . .
H H19A 0.6882 0.6227 0.3171 0.093 Uiso calc R 1 . .
C C20A 0.52801(19) 0.47928(15) 0.27791(12) 0.0677(5) Uani d . 1 . .
H H20A 0.5402 0.4569 0.3313 0.081 Uiso calc R 1 . .
C C21A 0.6824(3) 0.75565(19) 0.11292(18) 0.0952(7) Uani d . 1 . .
H H21A 0.7529 0.8271 0.1218 0.143 Uiso calc R 1 . .
H H21B 0.5942 0.7613 0.1038 0.143 Uiso calc R 1 . .
H H21C 0.6926 0.7062 0.0599 0.143 Uiso calc R 1 . .
C C22A 0.18238(19) 0.41711(14) 0.29253(14) 0.0676(5) Uani d . 1 . .
H H22A 0.2236 0.4264 0.3547 0.081 Uiso calc R 1 . .
H H22B 0.2404 0.4768 0.2691 0.081 Uiso calc R 1 . .
C C23A 0.0429(2) 0.42506(18) 0.29508(18) 0.0889(7) Uani d . 1 . .
H H23A 0.0523 0.4952 0.3335 0.133 Uiso calc R 1 . .
H H23B -0.0146 0.3671 0.3195 0.133 Uiso calc R 1 . .
H H23C 0.0024 0.4179 0.2340 0.133 Uiso calc R 1 . .
O O1B -0.01626(13) 0.72895(10) 0.53207(9) 0.0721(4) Uani d . 1 . .
O O2B 0.10372(17) 0.62330(13) -0.02416(10) 0.0924(5) Uani d . 1 . .
O O3B 0.65088(12) 1.43287(9) 0.47433(8) 0.0594(3) Uani d . 1 . .
N N1B 0.13486(14) 0.90123(11) 0.55429(11) 0.0560(3) Uani d . 1 . .
H H1B 0.1050(19) 0.9184(15) 0.6066(13) 0.068(5) Uiso d . 1 . .
N N5B 0.22122(13) 0.94024(10) 0.36776(10) 0.0496(3) Uani d . 1 . .
H H5B 0.2177(18) 0.9690(15) 0.3198(13) 0.063(5) Uiso d . 1 . .
C C2B 0.07613(17) 0.79736(13) 0.50562(12) 0.0540(4) Uani d . 1 . .
C C3B 0.12403(18) 0.76579(13) 0.41559(12) 0.0576(4) Uani d . 1 . .
H H3C 0.0724 0.6882 0.3878 0.069 Uiso calc R 1 . .
H H3D 0.2197 0.7752 0.4277 0.069 Uiso calc R 1 . .
C C4B 0.10920(15) 0.83176(12) 0.34669(11) 0.0504(4) Uani d . 1 . .
H H4B 0.0221 0.8429 0.3497 0.060 Uiso calc R 1 . .
C C6B 0.22491(15) 1.02343(12) 0.44994(10) 0.0468(3) Uani d . 1 . .
H H6B 0.1362 1.0323 0.4487 0.056 Uiso calc R 1 . .
C C7B 0.25490(15) 0.98713(12) 0.53712(11) 0.0492(3) Uani d . 1 A .
H H7B 0.3264 0.9563 0.5275 0.059 Uiso calc R 1 . .
C C8B 0.10992(16) 0.77287(12) 0.24925(12) 0.0537(4) Uani d . 1 . .
C C9B 0.1949(2) 0.71538(16) 0.22746(13) 0.0682(5) Uani d . 1 . .
H H9B 0.2532 0.7110 0.2744 0.082 Uiso calc R 1 . .
C C10B 0.1956(2) 0.66371(16) 0.13700(14) 0.0719(5) Uani d . 1 . .
H H10B 0.2527 0.6244 0.1239 0.086 Uiso calc R 1 . .
C C11B 0.1117(2) 0.67125(15) 0.06772(13) 0.0680(5) Uani d . 1 . .
C C12B 0.0291(2) 0.72951(17) 0.08731(14) 0.0760(5) Uani d . 1 . .
H H12B -0.0265 0.7360 0.0399 0.091 Uiso calc R 1 . .
C C13B 0.02760(19) 0.77921(15) 0.17759(13) 0.0663(5) Uani d . 1 . .
H H13B -0.0304 0.8178 0.1900 0.080 Uiso calc R 1 . .
C C14B 0.1884(3) 0.5635(2) -0.04813(17) 0.1003(8) Uani d . 1 . .
H H14D 0.1733 0.5350 -0.1136 0.150 Uiso calc R 1 . .
H H14E 0.1670 0.5034 -0.0189 0.150 Uiso calc R 1 . .
H H14F 0.2826 0.6111 -0.0282 0.150 Uiso calc R 1 . .
C C15B 0.33542(15) 1.13087(12) 0.44774(10) 0.0443(3) Uani d . 1 . .
C C16B 0.46146(15) 1.13398(12) 0.42465(11) 0.0494(4) Uani d . 1 . .
H H16B 0.4742 1.0679 0.4039 0.059 Uiso calc R 1 . .
C C17B 0.56951(15) 1.23233(12) 0.43144(11) 0.0492(4) Uani d . 1 . .
H H17B 0.6533 1.2321 0.4153 0.059 Uiso calc R 1 . .
C C18B 0.55133(15) 1.33051(12) 0.46237(10) 0.0459(3) Uani d . 1 . .
C C19B 0.42406(17) 1.32896(13) 0.48211(11) 0.0527(4) Uani d . 1 . .
H H19B 0.4103 1.3949 0.5006 0.063 Uiso calc R 1 . .
C C20B 0.31804(16) 1.23073(12) 0.47456(11) 0.0507(4) Uani d . 1 . .
H H20B 0.2330 1.2311 0.4877 0.061 Uiso calc R 1 . .
C C21B 0.78088(18) 1.44055(16) 0.45013(15) 0.0722(5) Uani d . 1 . .
H H21D 0.8395 1.5167 0.4619 0.108 Uiso calc R 1 . .
H H21E 0.7710 1.4059 0.3860 0.108 Uiso calc R 1 . .
H H21F 0.8205 1.4042 0.4860 0.108 Uiso calc R 1 . .
C C22B 0.30606(19) 1.08026(14) 0.62487(12) 0.0620(4) Uani d . 1 . .
H H22C 0.3794 1.1421 0.6134 0.074 Uiso calc PR 0.742(4) A 1
H H22D 0.2319 1.1048 0.6408 0.074 Uiso calc PR 0.742(4) A 1
H H22E 0.2589 1.1293 0.6198 0.074 Uiso d PR 0.258(4) A 2
H H22F 0.2763 1.0489 0.6753 0.074 Uiso d PR 0.258(4) A 2
C C23B 0.3575(3) 1.0464(3) 0.70459(18) 0.0822(10) Uani d P 0.742(4) A 1
H H23D 0.3885 1.1077 0.7577 0.123 Uiso calc PR 0.742(4) A 1
H H23E 0.4322 1.0234 0.6897 0.123 Uiso calc PR 0.742(4) A 1
H H23F 0.2848 0.9864 0.7173 0.123 Uiso calc PR 0.742(4) A 1
C C23C 0.4545(7) 1.1483(6) 0.6534(5) 0.068(2) Uani d P 0.258(4) A 2
H H23G 0.4667 1.2027 0.7096 0.102 Uiso calc PR 0.258(4) A 2
H H23H 0.4889 1.1845 0.6063 0.102 Uiso calc PR 0.258(4) A 2
H H23I 0.5035 1.1018 0.6628 0.102 Uiso calc PR 0.258(4) A 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11A O2A C14A . . 117.77(17) ?
C18A O3A C21A . . 118.48(17) ?
C2A N1A C7A . . 127.11(14) ?
C2A N1A H1A . . 115.7(12) ?
C7A N1A H1A . . 117.1(12) ?
C4A N5A C6A . . 115.07(11) ?
C4A N5A H5A . . 109.4(11) ?
C6A N5A H5A . . 107.9(11) ?
O1A C2A N1A . . 121.74(15) ?
O1A C2A C3A . . 120.31(15) ?
N1A C2A C3A . . 117.89(14) ?
C2A C3A C4A . . 112.81(14) ?
C2A C3A H3A . . 109.0 ?
C4A C3A H3A . . 109.0 ?
C2A C3A H3B . . 109.0 ?
C4A C3A H3B . . 109.0 ?
H3A C3A H3B . . 107.8 ?
N5A C4A C8A . . 109.97(11) ?
N5A C4A C3A . . 110.15(12) ?
C8A C4A C3A . . 111.13(12) ?
N5A C4A H4A . . 108.5 ?
C8A C4A H4A . . 108.5 ?
C3A C4A H4A . . 108.5 ?
N5A C6A C15A . . 108.36(11) ?
N5A C6A C7A . . 110.41(12) ?
C15A C6A C7A . . 112.49(12) ?
N5A C6A H6A . . 108.5 ?
C15A C6A H6A . . 108.5 ?
C7A C6A H6A . . 108.5 ?
N1A C7A C22A . . 106.99(13) ?
N1A C7A C6A . . 111.92(13) ?
C22A C7A C6A . . 113.26(13) ?
N1A C7A H7A . . 108.2 ?
C22A C7A H7A . . 108.2 ?
C6A C7A H7A . . 108.2 ?
C13A C8A C9A . . 117.36(14) ?
C13A C8A C4A . . 121.57(14) ?
C9A C8A C4A . . 121.05(14) ?
C10A C9A C8A . . 121.20(16) ?
C10A C9A H9A . . 119.4 ?
C8A C9A H9A . . 119.4 ?
C11A C10A C9A . . 120.46(15) ?
C11A C10A H10A . . 119.8 ?
C9A C10A H10A . . 119.8 ?
C10A C11A C12A . . 119.60(15) ?
C10A C11A O2A . . 115.66(16) ?
C12A C11A O2A . . 124.74(17) ?
C11A C12A C13A . . 119.48(16) ?
C11A C12A H12A . . 120.3 ?
C13A C12A H12A . . 120.3 ?
C8A C13A C12A . . 121.89(15) ?
C8A C13A H13A . . 119.1 ?
C12A C13A H13A . . 119.1 ?
O2A C14A H14A . . 109.5 ?
O2A C14A H14B . . 109.5 ?
H14A C14A H14B . . 109.5 ?
O2A C14A H14C . . 109.5 ?
H14A C14A H14C . . 109.5 ?
H14B C14A H14C . . 109.5 ?
C16A C15A C20A . . 116.87(15) ?
C16A C15A C6A . . 122.38(14) ?
C20A C15A C6A . . 120.73(14) ?
C15A C16A C17A . . 121.91(16) ?
C15A C16A H16A . . 119.0 ?
C17A C16A H16A . . 119.0 ?
C18A C17A C16A . . 119.78(17) ?
C18A C17A H17A . . 120.1 ?
C16A C17A H17A . . 120.1 ?
O3A C18A C17A . . 124.94(17) ?
O3A C18A C19A . . 115.86(16) ?
C17A C18A C19A . . 119.20(16) ?
C18A C19A C20A . . 120.19(17) ?
C18A C19A H19A . . 119.9 ?
C20A C19A H19A . . 119.9 ?
C19A C20A C15A . . 122.03(17) ?
C19A C20A H20A . . 119.0 ?
C15A C20A H20A . . 119.0 ?
O3A C21A H21A . . 109.5 ?
O3A C21A H21B . . 109.5 ?
H21A C21A H21B . . 109.5 ?
O3A C21A H21C . . 109.5 ?
H21A C21A H21C . . 109.5 ?
H21B C21A H21C . . 109.5 ?
C23A C22A C7A . . 113.26(16) ?
C23A C22A H22A . . 108.9 ?
C7A C22A H22A . . 108.9 ?
C23A C22A H22B . . 108.9 ?
C7A C22A H22B . . 108.9 ?
H22A C22A H22B . . 107.7 ?
C22A C23A H23A . . 109.5 ?
C22A C23A H23B . . 109.5 ?
H23A C23A H23B . . 109.5 ?
C22A C23A H23C . . 109.5 ?
H23A C23A H23C . . 109.5 ?
H23B C23A H23C . . 109.5 ?
C11B O2B C14B . . 117.88(19) ?
C18B O3B C21B . . 118.75(13) ?
C2B N1B C7B . . 127.36(14) ?
C2B N1B H1B . . 116.5(12) ?
C7B N1B H1B . . 115.7(12) ?
C6B N5B C4B . . 118.50(12) ?
C6B N5B H5B . . 107.2(12) ?
C4B N5B H5B . . 107.5(12) ?
O1B C2B N1B . . 121.57(15) ?
O1B C2B C3B . . 120.71(15) ?
N1B C2B C3B . . 117.70(14) ?
C2B C3B C4B . . 114.62(13) ?
C2B C3B H3C . . 108.6 ?
C4B C3B H3C . . 108.6 ?
C2B C3B H3D . . 108.6 ?
C4B C3B H3D . . 108.6 ?
H3C C3B H3D . . 107.6 ?
N5B C4B C8B . . 107.49(12) ?
N5B C4B C3B . . 111.39(14) ?
C8B C4B C3B . . 112.06(13) ?
N5B C4B H4B . . 108.6 ?
C8B C4B H4B . . 108.6 ?
C3B C4B H4B . . 108.6 ?
N5B C6B C15B . . 107.71(11) ?
N5B C6B C7B . . 110.00(12) ?
C15B C6B C7B . . 110.86(12) ?
N5B C6B H6B . . 109.4 ?
C15B C6B H6B . . 109.4 ?
C7B C6B H6B . . 109.4 ?
N1B C7B C22B . . 107.11(13) ?
N1B C7B C6B . . 112.21(13) ?
C22B C7B C6B . . 114.44(13) ?
N1B C7B H7B . . 107.6 ?
C22B C7B H7B . . 107.6 ?
C6B C7B H7B . . 107.6 ?
C13B C8B C9B . . 117.20(17) ?
C13B C8B C4B . . 119.98(15) ?
C9B C8B C4B . . 122.77(16) ?
C8B C9B C10B . . 121.68(19) ?
C8B C9B H9B . . 119.2 ?
C10B C9B H9B . . 119.2 ?
C11B C10B C9B . . 119.39(18) ?
C11B C10B H10B . . 120.3 ?
C9B C10B H10B . . 120.3 ?
C12B C11B C10B . . 120.02(18) ?
C12B C11B O2B . . 115.65(19) ?
C10B C11B O2B . . 124.33(19) ?
C11B C12B C13B . . 120.16(19) ?
C11B C12B H12B . . 119.9 ?
C13B C12B H12B . . 119.9 ?
C8B C13B C12B . . 121.54(18) ?
C8B C13B H13B . . 119.2 ?
C12B C13B H13B . . 119.2 ?
O2B C14B H14D . . 109.5 ?
O2B C14B H14E . . 109.5 ?
H14D C14B H14E . . 109.5 ?
O2B C14B H14F . . 109.5 ?
H14D C14B H14F . . 109.5 ?
H14E C14B H14F . . 109.5 ?
C16B C15B C20B . . 117.40(14) ?
C16B C15B C6B . . 120.88(12) ?
C20B C15B C6B . . 121.58(13) ?
C15B C16B C17B . . 122.12(13) ?
C15B C16B H16B . . 118.9 ?
C17B C16B H16B . . 118.9 ?
C18B C17B C16B . . 119.22(13) ?
C18B C17B H17B . . 120.4 ?
C16B C17B H17B . . 120.4 ?
O3B C18B C17B . . 124.78(14) ?
O3B C18B C19B . . 115.76(13) ?
C17B C18B C19B . . 119.45(14) ?
C20B C19B C18B . . 120.45(13) ?
C20B C19B H19B . . 119.8 ?
C18B C19B H19B . . 119.8 ?
C19B C20B C15B . . 121.22(14) ?
C19B C20B H20B . . 119.4 ?
C15B C20B H20B . . 119.4 ?
O3B C21B H21D . . 109.5 ?
O3B C21B H21E . . 109.5 ?
H21D C21B H21E . . 109.5 ?
O3B C21B H21F . . 109.5 ?
H21D C21B H21F . . 109.5 ?
H21E C21B H21F . . 109.5 ?
C23C C22B C23B . . 71.7(3) ?
C23C C22B C7B . . 121.4(3) ?
C23B C22B C7B . . 112.83(17) ?
C23C C22B H22C . . 37.5 ?
C23B C22B H22C . . 109.0 ?
C7B C22B H22C . . 109.0 ?
C23C C22B H22D . . 124.9 ?
C23B C22B H22D . . 109.0 ?
C7B C22B H22D . . 109.0 ?
H22C C22B H22D . . 107.8 ?
C23C C22B H22E . . 107.6 ?
C23B C22B H22E . . 133.3 ?
C7B C22B H22E . . 106.7 ?
H22C C22B H22E . . 79.3 ?
H22D C22B H22E . . 31.7 ?
C23C C22B H22F . . 105.9 ?
C23B C22B H22F . . 38.0 ?
C7B C22B H22F . . 107.6 ?
H22C C22B H22F . . 139.1 ?
H22D C22B H22F . . 76.2 ?
H22E C22B H22F . . 106.8 ?
C22B C23B H22F . . 38.5 ?
C22B C23B H23D . . 109.5 ?
H22F C23B H23D . . 105.4 ?
C22B C23B H23E . . 109.5 ?
H22F C23B H23E . . 140.1 ?
H23D C23B H23E . . 109.5 ?
C22B C23B H23F . . 109.5 ?
H22F C23B H23F . . 75.6 ?
H23D C23B H23F . . 109.5 ?
H23E C23B H23F . . 109.5 ?
C22B C23C H23G . . 109.5 ?
C22B C23C H23H . . 109.5 ?
H23G C23C H23H . . 109.5 ?
C22B C23C H23I . . 109.5 ?
H23G C23C H23I . . 109.5 ?
H23H C23C H23I . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C2A . 1.2323(19) ?
O2A C11A . 1.3725(19) ?
O2A C14A . 1.402(3) ?
O3A C18A . 1.365(2) ?
O3A C21A . 1.405(3) ?
N1A C2A . 1.330(2) ?
N1A C7A . 1.467(2) ?
N1A H1A . 0.881(19) ?
N5A C4A . 1.4642(19) ?
N5A C6A . 1.4717(19) ?
N5A H5A . 0.908(17) ?
C2A C3A . 1.498(2) ?
C3A C4A . 1.528(2) ?
C3A H3A . 0.97 ?
C3A H3B . 0.97 ?
C4A C8A . 1.506(2) ?
C4A H4A . 0.98 ?
C6A C15A . 1.510(2) ?
C6A C7A . 1.547(2) ?
C6A H6A . 0.98 ?
C7A C22A . 1.524(2) ?
C7A H7A . 0.98 ?
C8A C13A . 1.376(2) ?
C8A C9A . 1.382(2) ?
C9A C10A . 1.375(2) ?
C9A H9A . 0.93 ?
C10A C11A . 1.367(3) ?
C10A H10A . 0.93 ?
C11A C12A . 1.371(2) ?
C12A C13A . 1.381(2) ?
C12A H12A . 0.93 ?
C13A H13A . 0.93 ?
C14A H14A . 0.96 ?
C14A H14B . 0.96 ?
C14A H14C . 0.96 ?
C15A C16A . 1.372(2) ?
C15A C20A . 1.377(2) ?
C16A C17A . 1.386(2) ?
C16A H16A . 0.93 ?
C17A C18A . 1.368(3) ?
C17A H17A . 0.93 ?
C18A C19A . 1.371(3) ?
C19A C20A . 1.371(2) ?
C19A H19A . 0.93 ?
C20A H20A . 0.93 ?
C21A H21A . 0.96 ?
C21A H21B . 0.96 ?
C21A H21C . 0.96 ?
C22A C23A . 1.510(3) ?
C22A H22A . 0.97 ?
C22A H22B . 0.97 ?
C23A H23A . 0.96 ?
C23A H23B . 0.96 ?
C23A H23C . 0.96 ?
O1B C2B . 1.2341(18) ?
O2B C11B . 1.380(2) ?
O2B C14B . 1.405(3) ?
O3B C18B . 1.3698(18) ?
O3B C21B . 1.413(2) ?
N1B C2B . 1.328(2) ?
N1B C7B . 1.4621(19) ?
N1B H1B . 0.881(19) ?
N5B C6B . 1.4667(19) ?
N5B C4B . 1.4704(19) ?
N5B H5B . 0.890(19) ?
C2B C3B . 1.504(2) ?
C3B C4B . 1.527(2) ?
C3B H3C . 0.97 ?
C3B H3D . 0.97 ?
C4B C8B . 1.513(2) ?
C4B H4B . 0.98 ?
C6B C15B . 1.509(2) ?
C6B C7B . 1.541(2) ?
C6B H6B . 0.98 ?
C7B C22B . 1.528(2) ?
C7B H7B . 0.98 ?
C8B C13B . 1.375(2) ?
C8B C9B . 1.380(2) ?
C9B C10B . 1.393(3) ?
C9B H9B . 0.93 ?
C10B C11B . 1.366(3) ?
C10B H10B . 0.93 ?
C11B C12B . 1.361(3) ?
C12B C13B . 1.385(3) ?
C12B H12B . 0.93 ?
C13B H13B . 0.93 ?
C14B H14D . 0.96 ?
C14B H14E . 0.96 ?
C14B H14F . 0.96 ?
C15B C16B . 1.381(2) ?
C15B C20B . 1.388(2) ?
C16B C17B . 1.386(2) ?
C16B H16B . 0.93 ?
C17B C18B . 1.378(2) ?
C17B H17B . 0.93 ?
C18B C19B . 1.384(2) ?
C19B C20B . 1.372(2) ?
C19B H19B . 0.93 ?
C20B H20B . 0.93 ?
C21B H21D . 0.96 ?
C21B H21E . 0.96 ?
C21B H21F . 0.96 ?
C22B C23C . 1.488(7) ?
C22B C23B . 1.500(3) ?
C22B H22C . 0.97 ?
C22B H22D . 0.97 ?
C22B H22E . 0.96 ?
C22B H22F . 0.96 ?
C23B H22F . 0.95 ?
C23B H23D . 0.96 ?
C23B H23E . 0.96 ?
C23B H23F . 0.96 ?
C23C H23G . 0.96 ?
C23C H23H . 0.96 ?
C23C H23I . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1A H1A O1B 2_566 0.88(2) 2.21(2) 3.0833(19) 172(2)
N1B H1B O1A 2_566 0.88(2) 2.04(2) 2.9179(18) 175(2)
N5A H5A O2A 2_655 0.91(2) 2.49(2) 3.3769(18) 164(2)
C19B H19B O3B 2_686 0.93 2.56 3.477(2) 171
C20A H20A O3B 1_545 0.93 2.51 3.410(2) 162
C20B H20B O1B 2_576 0.93 2.53 3.398(2) 156
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7A N1A C2A O1A . . . . -178.83(17) ?
C7A N1A C2A C3A . . . . 4.0(3) ?
O1A C2A C3A C4A . . . . -115.07(19) ?
N1A C2A C3A C4A . . . . 62.1(2) ?
C6A N5A C4A C8A . . . . -162.77(12) ?
C6A N5A C4A C3A . . . . 74.42(16) ?
C2A C3A C4A N5A . . . . -84.26(16) ?
C2A C3A C4A C8A . . . . 153.62(14) ?
C4A N5A C6A C15A . . . . 165.11(12) ?
C4A N5A C6A C7A . . . . -71.27(16) ?
C2A N1A C7A C22A . . . . 170.41(17) ?
C2A N1A C7A C6A . . . . -65.0(2) ?
N5A C6A C7A N1A . . . . 77.41(16) ?
C15A C6A C7A N1A . . . . -161.40(13) ?
N5A C6A C7A C22A . . . . -161.54(14) ?
C15A C6A C7A C22A . . . . -40.34(19) ?
N5A C4A C8A C13A . . . . -62.46(18) ?
C3A C4A C8A C13A . . . . 59.77(19) ?
N5A C4A C8A C9A . . . . 119.32(15) ?
C3A C4A C8A C9A . . . . -118.45(16) ?
C13A C8A C9A C10A . . . . 1.0(2) ?
C4A C8A C9A C10A . . . . 179.28(14) ?
C8A C9A C10A C11A . . . . -1.0(2) ?
C9A C10A C11A C12A . . . . 0.1(2) ?
C9A C10A C11A O2A . . . . 179.98(14) ?
C14A O2A C11A C10A . . . . 179.67(18) ?
C14A O2A C11A C12A . . . . -0.5(3) ?
C10A C11A C12A C13A . . . . 0.7(2) ?
O2A C11A C12A C13A . . . . -179.17(15) ?
C9A C8A C13A C12A . . . . -0.2(2) ?
C4A C8A C13A C12A . . . . -178.45(14) ?
C11A C12A C13A C8A . . . . -0.7(3) ?
N5A C6A C15A C16A . . . . 53.58(19) ?
C7A C6A C15A C16A . . . . -68.77(19) ?
N5A C6A C15A C20A . . . . -127.96(17) ?
C7A C6A C15A C20A . . . . 109.69(18) ?
C20A C15A C16A C17A . . . . -1.0(3) ?
C6A C15A C16A C17A . . . . 177.51(16) ?
C15A C16A C17A C18A . . . . 0.1(3) ?
C21A O3A C18A C17A . . . . -0.3(3) ?
C21A O3A C18A C19A . . . . -179.81(19) ?
C16A C17A C18A O3A . . . . -178.51(17) ?
C16A C17A C18A C19A . . . . 0.9(3) ?
O3A C18A C19A C20A . . . . 178.55(18) ?
C17A C18A C19A C20A . . . . -0.9(3) ?
C18A C19A C20A C15A . . . . 0.0(3) ?
C16A C15A C20A C19A . . . . 1.0(3) ?
C6A C15A C20A C19A . . . . -177.55(18) ?
N1A C7A C22A C23A . . . . -62.2(2) ?
C6A C7A C22A C23A . . . . 173.98(16) ?
C7B N1B C2B O1B . . . . 172.26(16) ?
C7B N1B C2B C3B . . . . -8.9(3) ?
O1B C2B C3B C4B . . . . 120.58(17) ?
N1B C2B C3B C4B . . . . -58.2(2) ?
C6B N5B C4B C8B . . . . 166.79(13) ?
C6B N5B C4B C3B . . . . -70.10(17) ?
C2B C3B C4B N5B . . . . 79.81(17) ?
C2B C3B C4B C8B . . . . -159.73(14) ?
C4B N5B C6B C15B . . . . -171.56(13) ?
C4B N5B C6B C7B . . . . 67.51(17) ?
C2B N1B C7B C22B . . . . -164.28(16) ?
C2B N1B C7B C6B . . . . 69.3(2) ?
N5B C6B C7B N1B . . . . -76.30(15) ?
C15B C6B C7B N1B . . . . 164.68(12) ?
N5B C6B C7B C22B . . . . 161.37(13) ?
C15B C6B C7B C22B . . . . 42.35(17) ?
N5B C4B C8B C13B . . . . -93.95(17) ?
C3B C4B C8B C13B . . . . 143.35(16) ?
N5B C4B C8B C9B . . . . 83.29(19) ?
C3B C4B C8B C9B . . . . -39.4(2) ?
C13B C8B C9B C10B . . . . -1.4(3) ?
C4B C8B C9B C10B . . . . -178.68(16) ?
C8B C9B C10B C11B . . . . 1.0(3) ?
C9B C10B C11B C12B . . . . 0.5(3) ?
C9B C10B C11B O2B . . . . -179.86(17) ?
C14B O2B C11B C12B . . . . 179.14(19) ?
C14B O2B C11B C10B . . . . -0.5(3) ?
C10B C11B C12B C13B . . . . -1.5(3) ?
O2B C11B C12B C13B . . . . 178.86(17) ?
C9B C8B C13B C12B . . . . 0.4(3) ?
C4B C8B C13B C12B . . . . 177.77(16) ?
C11B C12B C13B C8B . . . . 1.0(3) ?
N5B C6B C15B C16B . . . . -43.91(19) ?
C7B C6B C15B C16B . . . . 76.49(17) ?
N5B C6B C15B C20B . . . . 140.46(15) ?
C7B C6B C15B C20B . . . . -99.15(16) ?
C20B C15B C16B C17B . . . . 2.8(2) ?
C6B C15B C16B C17B . . . . -173.01(14) ?
C15B C16B C17B C18B . . . . 0.1(2) ?
C21B O3B C18B C17B . . . . 2.8(2) ?
C21B O3B C18B C19B . . . . -176.19(15) ?
C16B C17B C18B O3B . . . . 178.24(14) ?
C16B C17B C18B C19B . . . . -2.8(2) ?
O3B C18B C19B C20B . . . . -178.41(14) ?
C17B C18B C19B C20B . . . . 2.6(2) ?
C18B C19B C20B C15B . . . . 0.4(2) ?
C16B C15B C20B C19B . . . . -3.1(2) ?
C6B C15B C20B C19B . . . . 172.70(14) ?
N1B C7B C22B C23C . . . . 146.9(4) ?
C6B C7B C22B C23C . . . . -88.0(4) ?
N1B C7B C22B C23B . . . . 65.1(2) ?
C6B C7B C22B C23B . . . . -169.84(18) ?
