#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/00/2230023.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_2230023
loop_
_publ_author_name
'Naicker, Tricia'
'Govender, Thavendran'
'Kruger, Hendrik G.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 (S)-2-Benzyl-N-(2,6-diisopropylphenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
;
_journal_coeditor_code           HG5021
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1106
_journal_paper_doi               10.1107/S1600536811012554
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C29 H34 N2 O'
_chemical_formula_moiety         'C29 H34 N2 O'
_chemical_formula_sum            'C29 H34 N2 O'
_chemical_formula_weight         426.58
_chemical_melting_point          419
_chemical_name_systematic
;(S)-2-Benzyl-N-(2,6-diisopropylphenyl)-1,2,3,4-
tetrahydroisoquinoline-3-carboxamide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.241(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.493(3)
_cell_length_b                   12.459(5)
_cell_length_c                   21.280(8)
_cell_measurement_reflns_used    16565
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      1.91
_cell_volume                     2459.6(16)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Kappa DUO APEXII'
_diffrn_measurement_method       '0.5° φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_av_sigmaI/netI    0.1071
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16565
_diffrn_reflns_theta_full        25.90
_diffrn_reflns_theta_max         25.90
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0643P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                2620
_reflns_number_total             4932
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5021.cif
_cod_data_source_block           I
_cod_original_cell_volume        2459.8(16)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2230023
_cod_database_fobs_code          2230023
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.4520(4) 0.3788(3) 0.7605(2) 0.0553(11) Uani d . 1 . .
N N1A 0.3190(4) 0.1660(3) 0.7484(2) 0.0400(11) Uani d . 1 . .
N N2A 0.2265(4) 0.4455(3) 0.7444(2) 0.0397(11) Uani d . 1 . .
H H2A 0.1342 0.4309 0.7402 0.048 Uiso calc R 1 . .
C C1A 0.2497(6) 0.0682(4) 0.7640(3) 0.0458(14) Uani d . 1 . .
H H1A1 0.3039 0.0059 0.7526 0.055 Uiso calc R 1 . .
H H1A2 0.1512 0.0650 0.7369 0.055 Uiso calc R 1 . .
C C2A 0.2389(6) 0.0573(4) 0.8331(3) 0.0428(13) Uani d . 1 . .
C C3A 0.1910(6) -0.0390(4) 0.8550(3) 0.0527(16) Uani d . 1 . .
H H3A 0.1676 -0.0975 0.8259 0.063 Uiso calc R 1 . .
C C4A 0.1770(8) -0.0512(6) 0.9181(4) 0.077(2) Uani d . 1 . .
H H4A 0.1432 -0.1169 0.9322 0.092 Uiso calc R 1 . .
C C5A 0.2131(9) 0.0344(5) 0.9607(3) 0.082(2) Uani d . 1 . .
H H5A 0.2061 0.0268 1.0043 0.098 Uiso calc R 1 . .
C C6A 0.2595(7) 0.1308(5) 0.9393(3) 0.0652(18) Uani d . 1 . .
H H6A 0.2835 0.1893 0.9682 0.078 Uiso calc R 1 . .
C C7A 0.2710(6) 0.1420(5) 0.8754(3) 0.0495(15) Uani d . 1 . .
C C8A 0.3150(6) 0.2485(4) 0.8519(3) 0.0505(15) Uani d . 1 . .
H H8A1 0.4212 0.2555 0.8639 0.061 Uiso calc R 1 . .
H H8A2 0.2725 0.3072 0.8732 0.061 Uiso calc R 1 . .
C C9A 0.2653(5) 0.2596(4) 0.7787(3) 0.0422(14) Uani d . 1 . .
H H9A 0.1575 0.2603 0.7671 0.051 Uiso calc R 1 . .
C C10A 0.3221(6) 0.3654(4) 0.7591(3) 0.0425(14) Uani d . 1 . .
C C11A 0.2686(5) 0.5540(4) 0.7353(3) 0.0375(13) Uani d . 1 . .
C C12A 0.3111(5) 0.6185(4) 0.7897(3) 0.0412(13) Uani d . 1 . .
C C13A 0.3565(6) 0.7229(4) 0.7806(3) 0.0494(15) Uani d . 1 . .
H H13A 0.3881 0.7682 0.8168 0.059 Uiso calc R 1 . .
C C14A 0.3559(5) 0.7612(4) 0.7194(3) 0.0457(14) Uani d . 1 . .
H H14A 0.3865 0.8325 0.7139 0.055 Uiso calc R 1 . .
C C15A 0.3109(5) 0.6961(4) 0.6664(3) 0.0433(14) Uani d . 1 . .
H H15A 0.3085 0.7239 0.6246 0.052 Uiso calc R 1 . .
C C16A 0.2686(5) 0.5892(4) 0.6732(3) 0.0392(13) Uani d . 1 . .
C C17A 0.3121(6) 0.5779(5) 0.8585(3) 0.0535(16) Uani d . 1 . .
H H17A 0.2544 0.5101 0.8537 0.064 Uiso calc R 1 . .
C C18A 0.2384(8) 0.6556(7) 0.8972(3) 0.085(2) Uani d . 1 . .
H H18A 0.1420 0.6734 0.8724 0.128 Uiso calc R 1 . .
H H18B 0.2959 0.7214 0.9061 0.128 Uiso calc R 1 . .
H H18C 0.2304 0.6218 0.9379 0.128 Uiso calc R 1 . .
C C19A 0.4627(7) 0.5488(6) 0.8949(3) 0.082(2) Uani d . 1 . .
H H19A 0.5068 0.4990 0.8690 0.122 Uiso calc R 1 . .
H H19B 0.4570 0.5146 0.9357 0.122 Uiso calc R 1 . .
H H19C 0.5215 0.6139 0.9033 0.122 Uiso calc R 1 . .
C C20A 0.2224(5) 0.5200(4) 0.6144(3) 0.0446(14) Uani d . 1 . .
H H20A 0.2029 0.4466 0.6296 0.054 Uiso calc R 1 . .
C C21A 0.0830(7) 0.5606(6) 0.5725(3) 0.078(2) Uani d . 1 . .
H H21A 0.0555 0.5142 0.5347 0.116 Uiso calc R 1 . .
H H21B 0.0968 0.6341 0.5585 0.116 Uiso calc R 1 . .
H H21C 0.0066 0.5597 0.5970 0.116 Uiso calc R 1 . .
C C22A 0.3397(7) 0.5089(7) 0.5768(4) 0.100(3) Uani d . 1 . .
H H22A 0.3054 0.4635 0.5390 0.150 Uiso calc R 1 . .
H H22B 0.4250 0.4761 0.6040 0.150 Uiso calc R 1 . .
H H22C 0.3648 0.5800 0.5628 0.150 Uiso calc R 1 . .
C C23A 0.2944(6) 0.1801(4) 0.6783(3) 0.0432(13) Uani d . 1 . .
H H23A 0.3346 0.2501 0.6688 0.052 Uiso calc R 1 . .
H H23B 0.1894 0.1813 0.6601 0.052 Uiso calc R 1 . .
C C24A 0.3627(6) 0.0920(4) 0.6462(3) 0.0405(14) Uani d . 1 . .
C C25A 0.4969(5) 0.0471(4) 0.6742(3) 0.0423(13) Uani d . 1 . .
H H25A 0.5460 0.0692 0.7158 0.051 Uiso calc R 1 . .
C C26A 0.5571(6) -0.0294(4) 0.6408(3) 0.0485(15) Uani d . 1 . .
H H26A 0.6468 -0.0607 0.6605 0.058 Uiso calc R 1 . .
C C27A 0.4912(7) -0.0610(5) 0.5806(3) 0.0571(16) Uani d . 1 . .
H H27A 0.5355 -0.1132 0.5585 0.069 Uiso calc R 1 . .
C C28A 0.3621(7) -0.0179(5) 0.5520(3) 0.0591(17) Uani d . 1 . .
H H28A 0.3170 -0.0398 0.5098 0.071 Uiso calc R 1 . .
C C29A 0.2949(6) 0.0581(5) 0.5839(3) 0.0500(15) Uani d . 1 . .
H H29A 0.2038 0.0868 0.5637 0.060 Uiso calc R 1 . .
O O1B 0.9234(4) 0.5025(3) 0.7158(2) 0.0623(12) Uani d . 1 . .
N N1B 0.7631(5) 0.6965(3) 0.7506(2) 0.0427(11) Uani d . 1 . .
N N2B 0.7236(4) 0.4144(3) 0.7293(2) 0.0413(11) Uani d . 1 . .
H H2B 0.6326 0.4217 0.7315 0.050 Uiso calc R 1 . .
C C1B 0.8992(6) 0.7412(4) 0.7392(3) 0.0485(15) Uani d . 1 . .
H H1B1 0.9780 0.6891 0.7537 0.058 Uiso calc R 1 . .
H H1B2 0.9229 0.8077 0.7647 0.058 Uiso calc R 1 . .
C C2B 0.8889(5) 0.7660(4) 0.6694(3) 0.0410(13) Uani d . 1 . .
C C3B 0.9876(6) 0.8381(4) 0.6513(3) 0.0535(16) Uani d . 1 . .
H H3B 1.0591 0.8712 0.6835 0.064 Uiso calc R 1 . .
C C4B 0.9815(7) 0.8613(5) 0.5870(3) 0.0597(17) Uani d . 1 . .
H H4B 1.0485 0.9103 0.5754 0.072 Uiso calc R 1 . .
C C5B 0.8789(7) 0.8137(6) 0.5401(3) 0.0625(18) Uani d . 1 . .
H H5B 0.8746 0.8290 0.4960 0.075 Uiso calc R 1 . .
C C6B 0.7813(6) 0.7425(5) 0.5579(3) 0.0540(16) Uani d . 1 . .
H H6B 0.7099 0.7095 0.5256 0.065 Uiso calc R 1 . .
C C7B 0.7866(5) 0.7187(4) 0.6224(3) 0.0411(14) Uani d . 1 . .
C C8B 0.6736(6) 0.6440(5) 0.6385(3) 0.0497(15) Uani d . 1 . .
H H8B1 0.6664 0.5799 0.6106 0.060 Uiso calc R 1 . .
H H8B2 0.5790 0.6809 0.6286 0.060 Uiso calc R 1 . .
C C9B 0.7039(5) 0.6072(4) 0.7090(3) 0.0438(14) Uani d . 1 . .
H H9B 0.6086 0.5892 0.7192 0.053 Uiso calc R 1 . .
C C10B 0.7946(5) 0.5040(4) 0.7188(3) 0.0444(14) Uani d . 1 . .
C C11B 0.7836(5) 0.3064(4) 0.7372(3) 0.0388(14) Uani d . 1 . .
C C12B 0.7980(5) 0.2485(4) 0.6820(3) 0.0380(13) Uani d . 1 . .
C C13B 0.8478(5) 0.1430(4) 0.6905(3) 0.0440(14) Uani d . 1 . .
H H13B 0.8625 0.1027 0.6545 0.053 Uiso calc R 1 . .
C C14B 0.8759(5) 0.0963(4) 0.7511(3) 0.0468(15) Uani d . 1 . .
H H14B 0.9048 0.0232 0.7558 0.056 Uiso calc R 1 . .
C C15B 0.8624(5) 0.1554(4) 0.8049(3) 0.0458(14) Uani d . 1 . .
H H15B 0.8857 0.1235 0.8463 0.055 Uiso calc R 1 . .
C C16B 0.8145(5) 0.2617(4) 0.7980(3) 0.0424(13) Uani d . 1 . .
C C17B 0.7624(5) 0.2969(4) 0.6148(3) 0.0448(14) Uani d . 1 . .
H H17B 0.7483 0.3759 0.6193 0.054 Uiso calc R 1 . .
C C18B 0.6219(7) 0.2505(7) 0.5757(3) 0.097(3) Uani d . 1 . .
H H18D 0.6012 0.2824 0.5327 0.145 Uiso calc R 1 . .
H H18E 0.5429 0.2668 0.5973 0.145 Uiso calc R 1 . .
H H18F 0.6314 0.1725 0.5722 0.145 Uiso calc R 1 . .
C C19B 0.8836(7) 0.2812(7) 0.5783(3) 0.091(3) Uani d . 1 . .
H H19D 0.8555 0.3134 0.5355 0.136 Uiso calc R 1 . .
H H19E 0.9012 0.2043 0.5741 0.136 Uiso calc R 1 . .
H H19F 0.9716 0.3158 0.6021 0.136 Uiso calc R 1 . .
C C20B 0.8034(6) 0.3296(5) 0.8566(3) 0.0508(15) Uani d . 1 . .
H H20B 0.7239 0.3827 0.8428 0.061 Uiso calc R 1 . .
C C21B 0.9450(7) 0.3931(6) 0.8793(3) 0.082(2) Uani d . 1 . .
H H21D 0.9377 0.4371 0.9166 0.123 Uiso calc R 1 . .
H H21E 0.9615 0.4396 0.8444 0.123 Uiso calc R 1 . .
H H21F 1.0257 0.3428 0.8912 0.123 Uiso calc R 1 . .
C C22B 0.7676(8) 0.2633(6) 0.9117(3) 0.076(2) Uani d . 1 . .
H H22D 0.7612 0.3109 0.9477 0.115 Uiso calc R 1 . .
H H22E 0.8435 0.2100 0.9259 0.115 Uiso calc R 1 . .
H H22F 0.6751 0.2267 0.8969 0.115 Uiso calc R 1 . .
C C23B 0.7704(7) 0.6783(5) 0.8191(3) 0.0601(17) Uani d . 1 . .
H H23C 0.8641 0.6446 0.8383 0.072 Uiso calc R 1 . .
H H23D 0.6933 0.6274 0.8241 0.072 Uiso calc R 1 . .
C C24B 0.7541(6) 0.7802(5) 0.8557(3) 0.0501(15) Uani d . 1 . .
C C25B 0.8105(9) 0.7866(6) 0.9212(4) 0.084(2) Uani d . 1 . .
H H25B 0.8687 0.7302 0.9428 0.101 Uiso calc R 1 . .
C C26B 0.7811(11) 0.8770(8) 0.9553(4) 0.112(3) Uani d . 1 . .
H H26B 0.8192 0.8812 1.0003 0.135 Uiso calc R 1 . .
C C27B 0.6978(10) 0.9599(7) 0.9248(4) 0.097(3) Uani d . 1 . .
H H27B 0.6766 1.0195 0.9490 0.116 Uiso calc R 1 . .
C C28B 0.6461(7) 0.9569(5) 0.8606(4) 0.0690(19) Uani d . 1 . .
H H28B 0.5914 1.0154 0.8396 0.083 Uiso calc R 1 . .
C C29B 0.6732(6) 0.8677(5) 0.8251(3) 0.0543(16) Uani d . 1 . .
H H29B 0.6369 0.8660 0.7799 0.065 Uiso calc R 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C1A N1A C23A . . 110.5(4) ?
C1A N1A C9A . . 110.3(4) ?
C23A N1A C9A . . 110.8(4) ?
C10A N2A C11A . . 122.6(4) ?
C10A N2A H2A . . 118.7 ?
C11A N2A H2A . . 118.7 ?
N1A C1A C2A . . 115.3(4) ?
N1A C1A H1A1 . . 108.4 ?
C2A C1A H1A1 . . 108.4 ?
N1A C1A H1A2 . . 108.4 ?
C2A C1A H1A2 . . 108.4 ?
H1A1 C1A H1A2 . . 107.5 ?
C7A C2A C3A . . 118.9(5) ?
C7A C2A C1A . . 121.2(5) ?
C3A C2A C1A . . 119.9(5) ?
C4A C3A C2A . . 121.4(6) ?
C4A C3A H3A . . 119.3 ?
C2A C3A H3A . . 119.3 ?
C3A C4A C5A . . 119.0(6) ?
C3A C4A H4A . . 120.5 ?
C5A C4A H4A . . 120.5 ?
C6A C5A C4A . . 120.0(6) ?
C6A C5A H5A . . 120.0 ?
C4A C5A H5A . . 120.0 ?
C5A C6A C7A . . 120.2(6) ?
C5A C6A H6A . . 119.9 ?
C7A C6A H6A . . 119.9 ?
C2A C7A C6A . . 120.5(5) ?
C2A C7A C8A . . 119.7(5) ?
C6A C7A C8A . . 119.8(5) ?
C7A C8A C9A . . 111.7(5) ?
C7A C8A H8A1 . . 109.3 ?
C9A C8A H8A1 . . 109.3 ?
C7A C8A H8A2 . . 109.3 ?
C9A C8A H8A2 . . 109.3 ?
H8A1 C8A H8A2 . . 107.9 ?
N1A C9A C10A . . 113.0(4) ?
N1A C9A C8A . . 108.2(4) ?
C10A C9A C8A . . 107.9(4) ?
N1A C9A H9A . . 109.2 ?
C10A C9A H9A . . 109.2 ?
C8A C9A H9A . . 109.2 ?
O1A C10A N2A . . 121.8(5) ?
O1A C10A C9A . . 121.4(5) ?
N2A C10A C9A . . 116.7(4) ?
C16A C11A C12A . . 123.2(5) ?
C16A C11A N2A . . 118.7(5) ?
C12A C11A N2A . . 118.1(5) ?
C11A C12A C13A . . 117.7(5) ?
C11A C12A C17A . . 122.6(5) ?
C13A C12A C17A . . 119.7(5) ?
C14A C13A C12A . . 120.7(6) ?
C14A C13A H13A . . 119.7 ?
C12A C13A H13A . . 119.7 ?
C15A C14A C13A . . 120.3(5) ?
C15A C14A H14A . . 119.8 ?
C13A C14A H14A . . 119.8 ?
C14A C15A C16A . . 121.1(5) ?
C14A C15A H15A . . 119.5 ?
C16A C15A H15A . . 119.5 ?
C11A C16A C15A . . 117.0(5) ?
C11A C16A C20A . . 123.4(4) ?
C15A C16A C20A . . 119.7(5) ?
C19A C17A C18A . . 111.4(5) ?
C19A C17A C12A . . 112.2(5) ?
C18A C17A C12A . . 113.0(5) ?
C19A C17A H17A . . 106.6 ?
C18A C17A H17A . . 106.6 ?
C12A C17A H17A . . 106.6 ?
C17A C18A H18A . . 109.5 ?
C17A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C17A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
C17A C19A H19A . . 109.5 ?
C17A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
C17A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C16A C20A C22A . . 112.1(4) ?
C16A C20A C21A . . 111.2(4) ?
C22A C20A C21A . . 111.5(6) ?
C16A C20A H20A . . 107.2 ?
C22A C20A H20A . . 107.2 ?
C21A C20A H20A . . 107.2 ?
C20A C21A H21A . . 109.5 ?
C20A C21A H21B . . 109.5 ?
H21A C21A H21B . . 109.5 ?
C20A C21A H21C . . 109.5 ?
H21A C21A H21C . . 109.5 ?
H21B C21A H21C . . 109.5 ?
C20A C22A H22A . . 109.5 ?
C20A C22A H22B . . 109.5 ?
H22A C22A H22B . . 109.5 ?
C20A C22A H22C . . 109.5 ?
H22A C22A H22C . . 109.5 ?
H22B C22A H22C . . 109.5 ?
N1A C23A C24A . . 112.4(4) ?
N1A C23A H23A . . 109.1 ?
C24A C23A H23A . . 109.1 ?
N1A C23A H23B . . 109.1 ?
C24A C23A H23B . . 109.1 ?
H23A C23A H23B . . 107.9 ?
C25A C24A C29A . . 118.2(5) ?
C25A C24A C23A . . 122.4(5) ?
C29A C24A C23A . . 119.3(5) ?
C26A C25A C24A . . 119.5(5) ?
C26A C25A H25A . . 120.2 ?
C24A C25A H25A . . 120.2 ?
C27A C26A C25A . . 121.8(5) ?
C27A C26A H26A . . 119.1 ?
C25A C26A H26A . . 119.1 ?
C28A C27A C26A . . 119.8(6) ?
C28A C27A H27A . . 120.1 ?
C26A C27A H27A . . 120.1 ?
C27A C28A C29A . . 120.9(6) ?
C27A C28A H28A . . 119.6 ?
C29A C28A H28A . . 119.6 ?
C28A C29A C24A . . 119.7(5) ?
C28A C29A H29A . . 120.2 ?
C24A C29A H29A . . 120.2 ?
C9B N1B C23B . . 114.7(4) ?
C9B N1B C1B . . 115.2(4) ?
C23B N1B C1B . . 111.4(4) ?
C10B N2B C11B . . 126.0(4) ?
C10B N2B H2B . . 117.0 ?
C11B N2B H2B . . 117.0 ?
N1B C1B C2B . . 111.5(4) ?
N1B C1B H1B1 . . 109.3 ?
C2B C1B H1B1 . . 109.3 ?
N1B C1B H1B2 . . 109.3 ?
C2B C1B H1B2 . . 109.3 ?
H1B1 C1B H1B2 . . 108.0 ?
C7B C2B C3B . . 118.9(5) ?
C7B C2B C1B . . 121.5(5) ?
C3B C2B C1B . . 119.7(5) ?
C4B C3B C2B . . 120.8(6) ?
C4B C3B H3B . . 119.6 ?
C2B C3B H3B . . 119.6 ?
C5B C4B C3B . . 120.1(6) ?
C5B C4B H4B . . 120.0 ?
C3B C4B H4B . . 120.0 ?
C4B C5B C6B . . 119.2(6) ?
C4B C5B H5B . . 120.4 ?
C6B C5B H5B . . 120.4 ?
C5B C6B C7B . . 121.1(6) ?
C5B C6B H6B . . 119.4 ?
C7B C6B H6B . . 119.4 ?
C2B C7B C6B . . 120.0(5) ?
C2B C7B C8B . . 121.6(5) ?
C6B C7B C8B . . 118.4(5) ?
C7B C8B C9B . . 114.2(4) ?
C7B C8B H8B1 . . 108.7 ?
C9B C8B H8B1 . . 108.7 ?
C7B C8B H8B2 . . 108.7 ?
C9B C8B H8B2 . . 108.7 ?
H8B1 C8B H8B2 . . 107.6 ?
N1B C9B C8B . . 109.5(4) ?
N1B C9B C10B . . 115.1(4) ?
C8B C9B C10B . . 111.5(5) ?
N1B C9B H9B . . 106.8 ?
C8B C9B H9B . . 106.8 ?
C10B C9B H9B . . 106.8 ?
O1B C10B N2B . . 122.0(5) ?
O1B C10B C9B . . 122.4(5) ?
N2B C10B C9B . . 115.5(4) ?
C16B C11B C12B . . 122.4(5) ?
C16B C11B N2B . . 118.8(5) ?
C12B C11B N2B . . 118.7(5) ?
C13B C12B C11B . . 117.6(5) ?
C13B C12B C17B . . 119.8(5) ?
C11B C12B C17B . . 122.7(4) ?
C14B C13B C12B . . 120.6(5) ?
C14B C13B H13B . . 119.7 ?
C12B C13B H13B . . 119.7 ?
C13B C14B C15B . . 120.7(5) ?
C13B C14B H14B . . 119.7 ?
C15B C14B H14B . . 119.7 ?
C14B C15B C16B . . 120.1(5) ?
C14B C15B H15B . . 120.0 ?
C16B C15B H15B . . 120.0 ?
C11B C16B C15B . . 118.6(5) ?
C11B C16B C20B . . 120.2(5) ?
C15B C16B C20B . . 121.1(5) ?
C12B C17B C18B . . 110.8(4) ?
C12B C17B C19B . . 112.6(5) ?
C18B C17B C19B . . 109.9(6) ?
C12B C17B H17B . . 107.8 ?
C18B C17B H17B . . 107.8 ?
C19B C17B H17B . . 107.8 ?
C17B C18B H18D . . 109.5 ?
C17B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C17B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
C17B C19B H19D . . 109.5 ?
C17B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C17B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
C16B C20B C22B . . 113.1(5) ?
C16B C20B C21B . . 109.4(4) ?
C22B C20B C21B . . 110.8(5) ?
C16B C20B H20B . . 107.8 ?
C22B C20B H20B . . 107.8 ?
C21B C20B H20B . . 107.8 ?
C20B C21B H21D . . 109.5 ?
C20B C21B H21E . . 109.5 ?
H21D C21B H21E . . 109.5 ?
C20B C21B H21F . . 109.5 ?
H21D C21B H21F . . 109.5 ?
H21E C21B H21F . . 109.5 ?
C20B C22B H22D . . 109.5 ?
C20B C22B H22E . . 109.5 ?
H22D C22B H22E . . 109.5 ?
C20B C22B H22F . . 109.5 ?
H22D C22B H22F . . 109.5 ?
H22E C22B H22F . . 109.5 ?
N1B C23B C24B . . 113.2(5) ?
N1B C23B H23C . . 108.9 ?
C24B C23B H23C . . 108.9 ?
N1B C23B H23D . . 108.9 ?
C24B C23B H23D . . 108.9 ?
H23C C23B H23D . . 107.7 ?
C25B C24B C29B . . 118.5(6) ?
C25B C24B C23B . . 120.4(6) ?
C29B C24B C23B . . 121.0(5) ?
C24B C25B C26B . . 119.4(7) ?
C24B C25B H25B . . 120.3 ?
C26B C25B H25B . . 120.3 ?
C27B C26B C25B . . 121.1(7) ?
C27B C26B H26B . . 119.4 ?
C25B C26B H26B . . 119.4 ?
C28B C27B C26B . . 120.4(7) ?
C28B C27B H27B . . 119.8 ?
C26B C27B H27B . . 119.8 ?
C27B C28B C29B . . 119.9(7) ?
C27B C28B H28B . . 120.0 ?
C29B C28B H28B . . 120.0 ?
C28B C29B C24B . . 120.6(6) ?
C28B C29B H29B . . 119.7 ?
C24B C29B H29B . . 119.7 ?
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 C10A . 1.238(6) ?
N1A C1A . 1.456(6) ?
N1A C23A . 1.470(6) ?
N1A C9A . 1.475(6) ?
N2A C10A . 1.341(6) ?
N2A C11A . 1.435(6) ?
N2A H2A . 0.8800 ?
C1A C2A . 1.502(7) ?
C1A H1A1 . 0.9900 ?
C1A H1A2 . 0.9900 ?
C2A C7A . 1.379(8) ?
C2A C3A . 1.397(7) ?
C3A C4A . 1.387(8) ?
C3A H3A . 0.9500 ?
C4A C5A . 1.394(9) ?
C4A H4A . 0.9500 ?
C5A C6A . 1.390(9) ?
C5A H5A . 0.9500 ?
C6A C7A . 1.392(8) ?
C6A H6A . 0.9500 ?
C7A C8A . 1.508(8) ?
C8A C9A . 1.535(7) ?
C8A H8A1 . 0.9900 ?
C8A H8A2 . 0.9900 ?
C9A C10A . 1.516(7) ?
C9A H9A . 1.0000 ?
C11A C16A . 1.392(7) ?
C11A C12A . 1.395(8) ?
C12A C13A . 1.397(7) ?
C12A C17A . 1.547(7) ?
C13A C14A . 1.385(8) ?
C13A H13A . 0.9500 ?
C14A C15A . 1.381(7) ?
C14A H14A . 0.9500 ?
C15A C16A . 1.408(7) ?
C15A H15A . 0.9500 ?
C16A C20A . 1.506(7) ?
C17A C19A . 1.518(9) ?
C17A C18A . 1.533(8) ?
C17A H17A . 1.0000 ?
C18A H18A . 0.9800 ?
C18A H18B . 0.9800 ?
C18A H18C . 0.9800 ?
C19A H19A . 0.9800 ?
C19A H19B . 0.9800 ?
C19A H19C . 0.9800 ?
C20A C22A . 1.510(7) ?
C20A C21A . 1.518(8) ?
C20A H20A . 1.0000 ?
C21A H21A . 0.9800 ?
C21A H21B . 0.9800 ?
C21A H21C . 0.9800 ?
C22A H22A . 0.9800 ?
C22A H22B . 0.9800 ?
C22A H22C . 0.9800 ?
C23A C24A . 1.510(7) ?
C23A H23A . 0.9900 ?
C23A H23B . 0.9900 ?
C24A C25A . 1.403(7) ?
C24A C29A . 1.410(8) ?
C25A C26A . 1.383(7) ?
C25A H25A . 0.9500 ?
C26A C27A . 1.360(8) ?
C26A H26A . 0.9500 ?
C27A C28A . 1.358(8) ?
C27A H27A . 0.9500 ?
C28A C29A . 1.396(8) ?
C28A H28A . 0.9500 ?
C29A H29A . 0.9500 ?
O1B C10B . 1.239(5) ?
N1B C9B . 1.458(7) ?
N1B C23B . 1.463(7) ?
N1B C1B . 1.474(6) ?
N2B C10B . 1.347(6) ?
N2B C11B . 1.457(6) ?
N2B H2B . 0.8800 ?
C1B C2B . 1.499(7) ?
C1B H1B1 . 0.9900 ?
C1B H1B2 . 0.9900 ?
C2B C7B . 1.371(7) ?
C2B C3B . 1.410(7) ?
C3B C4B . 1.388(8) ?
C3B H3B . 0.9500 ?
C4B C5B . 1.373(9) ?
C4B H4B . 0.9500 ?
C5B C6B . 1.393(8) ?
C5B H5B . 0.9500 ?
C6B C7B . 1.393(8) ?
C6B H6B . 0.9500 ?
C7B C8B . 1.514(7) ?
C8B C9B . 1.536(8) ?
C8B H8B1 . 0.9900 ?
C8B H8B2 . 0.9900 ?
C9B C10B . 1.537(7) ?
C9B H9B . 1.0000 ?
C11B C16B . 1.382(7) ?
C11B C12B . 1.410(7) ?
C12B C13B . 1.397(7) ?
C12B C17B . 1.523(7) ?
C13B C14B . 1.387(7) ?
C13B H13B . 0.9500 ?
C14B C15B . 1.389(7) ?
C14B H14B . 0.9500 ?
C15B C16B . 1.398(8) ?
C15B H15B . 0.9500 ?
C16B C20B . 1.528(7) ?
C17B C18B . 1.528(8) ?
C17B C19B . 1.530(7) ?
C17B H17B . 1.0000 ?
C18B H18D . 0.9800 ?
C18B H18E . 0.9800 ?
C18B H18F . 0.9800 ?
C19B H19D . 0.9800 ?
C19B H19E . 0.9800 ?
C19B H19F . 0.9800 ?
C20B C22B . 1.532(8) ?
C20B C21B . 1.546(8) ?
C20B H20B . 1.0000 ?
C21B H21D . 0.9800 ?
C21B H21E . 0.9800 ?
C21B H21F . 0.9800 ?
C22B H22D . 0.9800 ?
C22B H22E . 0.9800 ?
C22B H22F . 0.9800 ?
C23B C24B . 1.514(8) ?
C23B H23C . 0.9900 ?
C23B H23D . 0.9900 ?
C24B C25B . 1.386(9) ?
C24B C29B . 1.411(8) ?
C25B C26B . 1.399(11) ?
C25B H25B . 0.9500 ?
C26B C27B . 1.377(12) ?
C26B H26B . 0.9500 ?
C27B C28B . 1.351(9) ?
C27B H27B . 0.9500 ?
C28B C29B . 1.398(8) ?
C28B H28B . 0.9500 ?
C29B H29B . 0.9500 ?
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
N2A H2A O1B 1_455 0.88 2.15 2.900(6) 142
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
C23A N1A C1A C2A . . . . -167.1(4) ?
C9A N1A C1A C2A . . . . -44.3(6) ?
N1A C1A C2A C7A . . . . 10.2(7) ?
N1A C1A C2A C3A . . . . -171.9(5) ?
C7A C2A C3A C4A . . . . -0.7(9) ?
C1A C2A C3A C4A . . . . -178.7(5) ?
C2A C3A C4A C5A . . . . -0.8(10) ?
C3A C4A C5A C6A . . . . 1.4(11) ?
C4A C5A C6A C7A . . . . -0.5(11) ?
C3A C2A C7A C6A . . . . 1.7(8) ?
C1A C2A C7A C6A . . . . 179.6(5) ?
C3A C2A C7A C8A . . . . -176.7(5) ?
C1A C2A C7A C8A . . . . 1.3(8) ?
C5A C6A C7A C2A . . . . -1.1(10) ?
C5A C6A C7A C8A . . . . 177.2(6) ?
C2A C7A C8A C9A . . . . 20.9(7) ?
C6A C7A C8A C9A . . . . -157.4(5) ?
C1A N1A C9A C10A . . . . -174.4(5) ?
C23A N1A C9A C10A . . . . -51.8(6) ?
C1A N1A C9A C8A . . . . 66.2(5) ?
C23A N1A C9A C8A . . . . -171.2(4) ?
C7A C8A C9A N1A . . . . -53.9(5) ?
C7A C8A C9A C10A . . . . -176.5(4) ?
C11A N2A C10A O1A . . . . -6.0(8) ?
C11A N2A C10A C9A . . . . 169.5(5) ?
N1A C9A C10A O1A . . . . -48.6(7) ?
C8A C9A C10A O1A . . . . 71.0(6) ?
N1A C9A C10A N2A . . . . 135.9(5) ?
C8A C9A C10A N2A . . . . -104.5(5) ?
C10A N2A C11A C16A . . . . 94.7(6) ?
C10A N2A C11A C12A . . . . -83.8(6) ?
C16A C11A C12A C13A . . . . -0.5(7) ?
N2A C11A C12A C13A . . . . 177.9(4) ?
C16A C11A C12A C17A . . . . -179.3(5) ?
N2A C11A C12A C17A . . . . -0.9(7) ?
C11A C12A C13A C14A . . . . 1.4(7) ?
C17A C12A C13A C14A . . . . -179.7(5) ?
C12A C13A C14A C15A . . . . -0.4(8) ?
C13A C14A C15A C16A . . . . -1.7(8) ?
C12A C11A C16A C15A . . . . -1.5(7) ?
N2A C11A C16A C15A . . . . -179.9(4) ?
C12A C11A C16A C20A . . . . -179.8(4) ?
N2A C11A C16A C20A . . . . 1.8(7) ?
C14A C15A C16A C11A . . . . 2.5(7) ?
C14A C15A C16A C20A . . . . -179.0(4) ?
C11A C12A C17A C19A . . . . 101.6(6) ?
C13A C12A C17A C19A . . . . -77.2(7) ?
C11A C12A C17A C18A . . . . -131.5(6) ?
C13A C12A C17A C18A . . . . 49.6(7) ?
C11A C16A C20A C22A . . . . -122.6(6) ?
C15A C16A C20A C22A . . . . 59.1(7) ?
C11A C16A C20A C21A . . . . 111.8(6) ?
C15A C16A C20A C21A . . . . -66.5(6) ?
C1A N1A C23A C24A . . . . -64.0(5) ?
C9A N1A C23A C24A . . . . 173.6(4) ?
N1A C23A C24A C25A . . . . -37.8(6) ?
N1A C23A C24A C29A . . . . 146.7(5) ?
C29A C24A C25A C26A . . . . -1.1(7) ?
C23A C24A C25A C26A . . . . -176.6(4) ?
C24A C25A C26A C27A . . . . 1.5(7) ?
C25A C26A C27A C28A . . . . -0.7(8) ?
C26A C27A C28A C29A . . . . -0.6(9) ?
C27A C28A C29A C24A . . . . 1.0(8) ?
C25A C24A C29A C28A . . . . -0.2(7) ?
C23A C24A C29A C28A . . . . 175.5(5) ?
C9B N1B C1B C2B . . . . 50.4(6) ?
C23B N1B C1B C2B . . . . -176.6(4) ?
N1B C1B C2B C7B . . . . -20.6(7) ?
N1B C1B C2B C3B . . . . 160.4(4) ?
C7B C2B C3B C4B . . . . 0.2(7) ?
C1B C2B C3B C4B . . . . 179.2(5) ?
C2B C3B C4B C5B . . . . -0.2(8) ?
C3B C4B C5B C6B . . . . 0.3(9) ?
C4B C5B C6B C7B . . . . -0.2(9) ?
C3B C2B C7B C6B . . . . -0.2(7) ?
C1B C2B C7B C6B . . . . -179.1(5) ?
C3B C2B C7B C8B . . . . -177.5(4) ?
C1B C2B C7B C8B . . . . 3.5(7) ?
C5B C6B C7B C2B . . . . 0.2(8) ?
C5B C6B C7B C8B . . . . 177.6(5) ?
C2B C7B C8B C9B . . . . -12.9(7) ?
C6B C7B C8B C9B . . . . 169.7(5) ?
C23B N1B C9B C8B . . . . 168.6(4) ?
C1B N1B C9B C8B . . . . -60.0(5) ?
C23B N1B C9B C10B . . . . -64.9(6) ?
C1B N1B C9B C10B . . . . 66.5(6) ?
C7B C8B C9B N1B . . . . 39.0(6) ?
C7B C8B C9B C10B . . . . -89.4(5) ?
C11B N2B C10B O1B . . . . -1.1(9) ?
C11B N2B C10B C9B . . . . 177.3(5) ?
N1B C9B C10B O1B . . . . -54.7(7) ?
C8B C9B C10B O1B . . . . 70.7(7) ?
N1B C9B C10B N2B . . . . 126.9(5) ?
C8B C9B C10B N2B . . . . -107.7(5) ?
C10B N2B C11B C16B . . . . 105.7(6) ?
C10B N2B C11B C12B . . . . -78.9(6) ?
C16B C11B C12B C13B . . . . -1.1(7) ?
N2B C11B C12B C13B . . . . -176.3(4) ?
C16B C11B C12B C17B . . . . 179.3(4) ?
N2B C11B C12B C17B . . . . 4.0(7) ?
C11B C12B C13B C14B . . . . 2.6(7) ?
C17B C12B C13B C14B . . . . -177.7(4) ?
C12B C13B C14B C15B . . . . -3.4(8) ?
C13B C14B C15B C16B . . . . 2.5(8) ?
C12B C11B C16B C15B . . . . 0.3(7) ?
N2B C11B C16B C15B . . . . 175.5(4) ?
C12B C11B C16B C20B . . . . 177.3(4) ?
N2B C11B C16B C20B . . . . -7.5(7) ?
C14B C15B C16B C11B . . . . -1.0(7) ?
C14B C15B C16B C20B . . . . -177.9(5) ?
C13B C12B C17B C18B . . . . 73.6(6) ?
C11B C12B C17B C18B . . . . -106.8(6) ?
C13B C12B C17B C19B . . . . -49.9(7) ?
C11B C12B C17B C19B . . . . 129.7(6) ?
C11B C16B C20B C22B . . . . 151.7(5) ?
C15B C16B C20B C22B . . . . -31.3(7) ?
C11B C16B C20B C21B . . . . -84.2(6) ?
C15B C16B C20B C21B . . . . 92.7(6) ?
C9B N1B C23B C24B . . . . -149.5(5) ?
C1B N1B C23B C24B . . . . 77.3(6) ?
N1B C23B C24B C25B . . . . -155.5(6) ?
N1B C23B C24B C29B . . . . 28.9(8) ?
C29B C24B C25B C26B . . . . 2.5(10) ?
C23B C24B C25B C26B . . . . -173.2(7) ?
C24B C25B C26B C27B . . . . -0.4(13) ?
C25B C26B C27B C28B . . . . -1.9(14) ?
C26B C27B C28B C29B . . . . 2.1(12) ?
C27B C28B C29B C24B . . . . 0.1(9) ?
C25B C24B C29B C28B . . . . -2.5(9) ?
C23B C24B C29B C28B . . . . 173.2(5) ?
