#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223211.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_2223211
loop_
_publ_author_name
'Zemama, Redwan Mohamed'
'Amari, Ibtissam'
'Bouhfid, Rachid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
1-Benzyl-3-[(dimethylamino)methylene]-4-phenyl-1H-1,4-benzodiazepin-2(3H)-one
_journal_coeditor_code           TK2525
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2160
_journal_paper_doi               10.1107/S1600536809031687
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C25 H23 N3 O'
_chemical_formula_moiety         'C25 H23 N3 O'
_chemical_formula_sum            'C25 H23 N3 O'
_chemical_formula_weight         381.46
_chemical_name_systematic
;
1-Benzyl-3-[(dimethylamino)methylene]-4-phenyl-1H-
1,4-benzodiazepin-2(3H)-one
;
_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
_cell_angle_beta                 115.6440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9733(3)
_cell_length_b                   26.3103(7)
_cell_length_c                   9.9312(3)
_cell_measurement_reflns_used    9099
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.3
_cell_volume                     2113.71(11)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'φ and ω'
_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  0.038
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25753
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         4959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0708P)²+0.1173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.118
_reflns_number_gt                4091
_reflns_number_total             4959
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2525.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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        2113.70(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2223211
_cod_database_fobs_code          2223211
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 O1 0.4567(3) 0.50001(9) 0.2429(3) 0.0798(8) Uani d . 1 . .
O O2 -0.0517(2) 0.22010(11) 0.2356(2) 0.0676(7) Uani d . 1 . .
N N1 0.7169(3) 0.47041(9) 0.3628(3) 0.0533(6) Uani d . 1 . .
N N2 0.7751(3) 0.38557(8) 0.2028(3) 0.0442(5) Uani d . 1 . .
N N3 0.2708(3) 0.35681(10) 0.1081(3) 0.0594(6) Uani d . 1 . .
N N4 0.2245(2) 0.21276(8) 0.3724(2) 0.0389(4) Uani d . 1 . .
N N5 0.3779(2) 0.14267(8) 0.2472(2) 0.0387(4) Uani d . 1 . .
N N6 -0.0202(3) 0.18176(10) -0.1543(2) 0.0542(6) Uani d . 1 . .
C C1 0.7741(4) 0.52148(12) 0.4267(4) 0.0659(9) Uani d . 1 . .
H H1A 0.7646 0.5244 0.5200 0.079 Uiso calc R 1 . .
H H1B 0.7023 0.5469 0.3587 0.079 Uiso calc R 1 . .
C C2 0.9491(4) 0.53244(11) 0.4550(3) 0.0554(7) Uani d . 1 . .
C C3 1.0522(6) 0.55963(16) 0.5788(5) 0.0892(13) Uani d . 1 . .
H H3 1.0140 0.5697 0.6480 0.107 Uiso calc R 1 . .
C C4 1.2105(7) 0.5723(2) 0.6026(7) 0.120(2) Uani d . 1 . .
H H4 1.2771 0.5908 0.6871 0.144 Uiso calc R 1 . .
C C5 1.2692(6) 0.5583(2) 0.5057(7) 0.1061(17) Uani d . 1 . .
H H5 1.3760 0.5672 0.5222 0.127 Uiso calc R 1 . .
C C6 1.1719(5) 0.53067(18) 0.3822(5) 0.0850(11) Uani d . 1 . .
H H6 1.2128 0.5204 0.3150 0.102 Uiso calc R 1 . .
C C7 1.0129(4) 0.51803(13) 0.3574(4) 0.0646(8) Uani d . 1 . .
H H7 0.9474 0.4994 0.2728 0.077 Uiso calc R 1 . .
C C8 0.8150(3) 0.42770(10) 0.4385(3) 0.0462(6) Uani d . 1 . .
C C9 0.8904(4) 0.42662(13) 0.5933(4) 0.0609(8) Uani d . 1 . .
H H9 0.8712 0.4529 0.6464 0.073 Uiso calc R 1 . .
C C10 0.9937(4) 0.38716(15) 0.6696(4) 0.0653(8) Uani d . 1 . .
H H10 1.0424 0.3867 0.7734 0.078 Uiso calc R 1 . .
C C11 1.0243(4) 0.34859(13) 0.5920(4) 0.0584(7) Uani d . 1 . .
H H11 1.0934 0.3219 0.6434 0.070 Uiso calc R 1 . .
C C12 0.9533(3) 0.34936(11) 0.4390(3) 0.0475(6) Uani d . 1 . .
H H12 0.9785 0.3238 0.3874 0.057 Uiso calc R 1 . .
C C13 0.8435(3) 0.38794(9) 0.3592(3) 0.0404(5) Uani d . 1 . .
C C14 0.6213(3) 0.39644(10) 0.1254(3) 0.0426(6) Uani d . 1 . .
C C15 0.5592(3) 0.39494(11) -0.0400(3) 0.0507(7) Uani d . 1 . .
C C16 0.6396(4) 0.36447(14) -0.1030(4) 0.0643(8) Uani d . 1 . .
H H16 0.7246 0.3430 -0.0427 0.077 Uiso calc R 1 . .
C C17 0.5928(6) 0.36622(19) -0.2549(5) 0.0898(14) Uani d . 1 . .
H H17 0.6471 0.3461 -0.2967 0.108 Uiso calc R 1 . .
C C18 0.4649(7) 0.3979(2) -0.3453(5) 0.0981(16) Uani d . 1 . .
H H18 0.4348 0.3993 -0.4474 0.118 Uiso calc R 1 . .
C C19 0.3842(6) 0.4266(2) -0.2859(5) 0.0903(14) Uani d . 1 . .
H H19 0.2975 0.4474 -0.3473 0.108 Uiso calc R 1 . .
C C20 0.4305(4) 0.42525(15) -0.1321(4) 0.0696(9) Uani d . 1 . .
H H20 0.3739 0.4450 -0.0918 0.084 Uiso calc R 1 . .
C C21 0.5079(3) 0.41522(11) 0.1880(3) 0.0473(6) Uani d . 1 . .
C C22 0.5557(3) 0.46494(11) 0.2668(4) 0.0531(7) Uani d . 1 . .
C C23 0.3567(3) 0.39855(12) 0.1694(3) 0.0522(7) Uani d . 1 . .
H H23 0.3030 0.4207 0.2069 0.063 Uiso calc R 1 . .
C C24 0.1156(4) 0.34505(16) 0.1107(5) 0.0756(10) Uani d . 1 . .
H H24A 0.0819 0.3731 0.1530 0.113 Uiso calc R 1 . .
H H24B 0.1279 0.3152 0.1703 0.113 Uiso calc R 1 . .
H H24C 0.0335 0.3390 0.0107 0.113 Uiso calc R 1 . .
C C25 0.3329(4) 0.31667(13) 0.0448(4) 0.0618(8) Uani d . 1 . .
H H25A 0.4515 0.3170 0.0918 0.093 Uiso calc R 1 . .
H H25B 0.2938 0.3222 -0.0606 0.093 Uiso calc R 1 . .
H H25C 0.2941 0.2843 0.0614 0.093 Uiso calc R 1 . .
C C26 0.2094(3) 0.22775(11) 0.5084(3) 0.0433(6) Uani d . 1 . .
H H26A 0.1039 0.2160 0.5017 0.052 Uiso calc R 1 . .
H H26B 0.2108 0.2645 0.5151 0.052 Uiso calc R 1 . .
C C27 0.3454(3) 0.20659(10) 0.6471(3) 0.0385(5) Uani d . 1 . .
C C28 0.4192(4) 0.23647(11) 0.7735(3) 0.0506(7) Uani d . 1 . .
H H28 0.3895 0.2705 0.7694 0.061 Uiso calc R 1 . .
C C29 0.5365(4) 0.21660(14) 0.9058(3) 0.0643(8) Uani d . 1 . .
H H29 0.5844 0.2371 0.9900 0.077 Uiso calc R 1 . .
C C30 0.5822(4) 0.16642(15) 0.9128(3) 0.0644(8) Uani d . 1 . .
H H30 0.6591 0.1527 1.0024 0.077 Uiso calc R 1 . .
C C31 0.5143(4) 0.13667(13) 0.7877(4) 0.0630(8) Uani d . 1 . .
H H31 0.5475 0.1030 0.7916 0.076 Uiso calc R 1 . .
C C32 0.3955(4) 0.15661(10) 0.6542(3) 0.0507(6) Uani d . 1 . .
H H32 0.3498 0.1362 0.5696 0.061 Uiso calc R 1 . .
C C33 0.3757(3) 0.22508(9) 0.3639(2) 0.0344(5) Uani d . 1 . .
C C34 0.4547(3) 0.27062(10) 0.4213(3) 0.0414(5) Uani d . 1 . .
H H34 0.4093 0.2930 0.4659 0.050 Uiso calc R 1 . .
C C35 0.6004(3) 0.28346(11) 0.4134(3) 0.0470(6) Uani d . 1 . .
H H35 0.6518 0.3143 0.4514 0.056 Uiso calc R 1 . .
C C36 0.6686(3) 0.24983(11) 0.3485(3) 0.0462(6) Uani d . 1 . .
H H36 0.7653 0.2584 0.3410 0.055 Uiso calc R 1 . .
C C37 0.5936(3) 0.20385(11) 0.2952(3) 0.0414(5) Uani d . 1 . .
H H37 0.6430 0.1810 0.2555 0.050 Uiso calc R 1 . .
C C38 0.4454(3) 0.19078(9) 0.2991(2) 0.0346(5) Uani d . 1 . .
C C39 0.2219(3) 0.13862(9) 0.1633(2) 0.0347(5) Uani d . 1 . .
C C40 0.1538(3) 0.08647(10) 0.1183(3) 0.0399(5) Uani d . 1 . .
C C41 0.2590(4) 0.04589(12) 0.1369(4) 0.0618(8) Uani d . 1 . .
H H41 0.3723 0.0513 0.1747 0.074 Uiso calc R 1 . .
C C42 0.1952(5) -0.00297(13) 0.0990(5) 0.0770(10) Uani d . 1 . .
H H42 0.2665 -0.0302 0.1126 0.092 Uiso calc R 1 . .
C C43 0.0313(5) -0.01128(13) 0.0430(4) 0.0743(10) Uani d . 1 . .
H H43 -0.0097 -0.0441 0.0168 0.089 Uiso calc R 1 . .
C C44 -0.0745(4) 0.02783(13) 0.0242(4) 0.0669(9) Uani d . 1 . .
H H44 -0.1875 0.0218 -0.0140 0.080 Uiso calc R 1 . .
C C45 -0.0137(4) 0.07677(11) 0.0622(3) 0.0526(7) Uani d . 1 . .
H H45 -0.0866 0.1034 0.0498 0.063 Uiso calc R 1 . .
C C46 0.1031(3) 0.18180(9) 0.1194(3) 0.0362(5) Uani d . 1 . .
C C47 0.0810(3) 0.20655(10) 0.2424(3) 0.0396(5) Uani d . 1 . .
C C48 -0.0072(3) 0.19553(10) -0.0206(3) 0.0424(6) Uani d . 1 . .
H H48 -0.0873 0.2185 -0.0233 0.051 Uiso calc R 1 . .
C C49 -0.1540(5) 0.2023(2) -0.2892(4) 0.0953(14) Uani d . 1 . .
H H49A -0.2265 0.2222 -0.2622 0.143 Uiso calc R 1 . .
H H49B -0.2149 0.1749 -0.3529 0.143 Uiso calc R 1 . .
H H49C -0.1084 0.2233 -0.3411 0.143 Uiso calc R 1 . .
C C50 0.0990(4) 0.15021(15) -0.1764(4) 0.0656(9) Uani d . 1 . .
H H50A 0.2077 0.1573 -0.0999 0.098 Uiso calc R 1 . .
H H50B 0.0957 0.1573 -0.2725 0.098 Uiso calc R 1 . .
H H50C 0.0729 0.1151 -0.1715 0.098 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
C22 N1 C8 . . 121.1(2) ?
C22 N1 C1 . . 117.8(2) ?
C8 N1 C1 . . 118.0(2) ?
C14 N2 C13 . . 119.6(2) ?
C23 N3 C24 . . 123.0(3) ?
C23 N3 C25 . . 122.9(3) ?
C24 N3 C25 . . 113.9(3) ?
C47 N4 C33 . . 119.68(19) ?
C47 N4 C26 . . 118.08(19) ?
C33 N4 C26 . . 117.39(19) ?
C39 N5 C38 . . 119.3(2) ?
C48 N6 C50 . . 123.8(2) ?
C48 N6 C49 . . 119.7(3) ?
C50 N6 C49 . . 116.2(3) ?
N1 C1 C2 . . 113.3(2) ?
N1 C1 H1A . . 108.9 ?
C2 C1 H1A . . 108.9 ?
N1 C1 H1B . . 108.9 ?
C2 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
C7 C2 C3 . . 116.7(4) ?
C7 C2 C1 . . 122.5(3) ?
C3 C2 C1 . . 120.8(4) ?
C4 C3 C2 . . 121.6(5) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C5 C4 C3 . . 120.7(5) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 119.7(5) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C7 . . 119.9(5) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C2 C7 C6 . . 121.4(4) ?
C2 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C9 C8 C13 . . 119.3(2) ?
C9 C8 N1 . . 119.7(3) ?
C13 C8 N1 . . 121.0(3) ?
C10 C9 C8 . . 121.0(3) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C11 C10 C9 . . 119.9(3) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C12 C11 C10 . . 120.1(3) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 121.0(3) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C8 C13 C12 . . 118.7(2) ?
C8 C13 N2 . . 123.9(2) ?
C12 C13 N2 . . 117.3(2) ?
N2 C14 C21 . . 125.0(2) ?
N2 C14 C15 . . 116.4(2) ?
C21 C14 C15 . . 118.2(2) ?
C20 C15 C16 . . 118.9(3) ?
C20 C15 C14 . . 121.6(3) ?
C16 C15 C14 . . 119.4(3) ?
C17 C16 C15 . . 119.9(4) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.2(4) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C19 C18 C17 . . 120.3(4) ?
C19 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C18 C19 C20 . . 120.1(4) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C15 C20 C19 . . 120.5(4) ?
C15 C20 H20 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C23 C21 C14 . . 131.2(3) ?
C23 C21 C22 . . 113.5(3) ?
C14 C21 C22 . . 114.7(2) ?
O1 C22 N1 . . 121.2(3) ?
O1 C22 C21 . . 122.5(3) ?
N1 C22 C21 . . 116.2(2) ?
N3 C23 C21 . . 132.5(3) ?
N3 C23 H23 . . 113.7 ?
C21 C23 H23 . . 113.7 ?
N3 C24 H24A . . 109.5 ?
N3 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
N3 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
N3 C25 H25A . . 109.5 ?
N3 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
N3 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
N4 C26 C27 . . 112.6(2) ?
N4 C26 H26A . . 109.1 ?
C27 C26 H26A . . 109.1 ?
N4 C26 H26B . . 109.1 ?
C27 C26 H26B . . 109.1 ?
H26A C26 H26B . . 107.8 ?
C28 C27 C32 . . 118.5(2) ?
C28 C27 C26 . . 120.2(2) ?
C32 C27 C26 . . 121.2(2) ?
C27 C28 C29 . . 121.1(3) ?
C27 C28 H28 . . 119.5 ?
C29 C28 H28 . . 119.5 ?
C30 C29 C28 . . 119.9(3) ?
C30 C29 H29 . . 120.0 ?
C28 C29 H29 . . 120.0 ?
C31 C30 C29 . . 119.8(3) ?
C31 C30 H30 . . 120.1 ?
C29 C30 H30 . . 120.1 ?
C30 C31 C32 . . 120.3(3) ?
C30 C31 H31 . . 119.8 ?
C32 C31 H31 . . 119.8 ?
C27 C32 C31 . . 120.3(3) ?
C27 C32 H32 . . 119.8 ?
C31 C32 H32 . . 119.8 ?
C34 C33 C38 . . 119.7(2) ?
C34 C33 N4 . . 120.1(2) ?
C38 C33 N4 . . 120.2(2) ?
C33 C34 C35 . . 121.1(2) ?
C33 C34 H34 . . 119.5 ?
C35 C34 H34 . . 119.5 ?
C36 C35 C34 . . 119.3(3) ?
C36 C35 H35 . . 120.4 ?
C34 C35 H35 . . 120.4 ?
C37 C36 C35 . . 120.1(2) ?
C37 C36 H36 . . 120.0 ?
C35 C36 H36 . . 120.0 ?
C36 C37 C38 . . 121.4(2) ?
C36 C37 H37 . . 119.3 ?
C38 C37 H37 . . 119.3 ?
C37 C38 N5 . . 118.6(2) ?
C37 C38 C33 . . 118.4(2) ?
N5 C38 C33 . . 122.8(2) ?
N5 C39 C46 . . 124.5(2) ?
N5 C39 C40 . . 117.5(2) ?
C46 C39 C40 . . 117.8(2) ?
C45 C40 C41 . . 118.1(3) ?
C45 C40 C39 . . 121.6(2) ?
C41 C40 C39 . . 120.2(2) ?
C40 C41 C42 . . 120.0(3) ?
C40 C41 H41 . . 120.0 ?
C42 C41 H41 . . 120.0 ?
C43 C42 C41 . . 120.7(3) ?
C43 C42 H42 . . 119.7 ?
C41 C42 H42 . . 119.7 ?
C42 C43 C44 . . 120.5(3) ?
C42 C43 H43 . . 119.7 ?
C44 C43 H43 . . 119.7 ?
C43 C44 C45 . . 119.9(3) ?
C43 C44 H44 . . 120.1 ?
C45 C44 H44 . . 120.1 ?
C40 C45 C44 . . 120.8(3) ?
C40 C45 H45 . . 119.6 ?
C44 C45 H45 . . 119.6 ?
C48 C46 C47 . . 115.5(2) ?
C48 C46 C39 . . 127.9(2) ?
C47 C46 C39 . . 115.57(19) ?
O2 C47 N4 . . 120.7(2) ?
O2 C47 C46 . . 124.4(2) ?
N4 C47 C46 . . 114.92(19) ?
N6 C48 C46 . . 131.1(3) ?
N6 C48 H48 . . 114.5 ?
C46 C48 H48 . . 114.5 ?
N6 C49 H49A . . 109.5 ?
N6 C49 H49B . . 109.5 ?
H49A C49 H49B . . 109.5 ?
N6 C49 H49C . . 109.5 ?
H49A C49 H49C . . 109.5 ?
H49B C49 H49C . . 109.5 ?
N6 C50 H50A . . 109.5 ?
N6 C50 H50B . . 109.5 ?
H50A C50 H50B . . 109.5 ?
N6 C50 H50C . . 109.5 ?
H50A C50 H50C . . 109.5 ?
H50B C50 H50C . . 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
O1 C22 . 1.231(3) ?
O2 C47 . 1.216(3) ?
N1 C22 . 1.352(4) ?
N1 C8 . 1.425(3) ?
N1 C1 . 1.480(4) ?
N2 C14 . 1.288(3) ?
N2 C13 . 1.403(3) ?
N3 C23 . 1.328(4) ?
N3 C24 . 1.438(4) ?
N3 C25 . 1.458(5) ?
N4 C47 . 1.383(3) ?
N4 C33 . 1.432(3) ?
N4 C26 . 1.469(3) ?
N5 C39 . 1.286(3) ?
N5 C38 . 1.402(3) ?
N6 C48 . 1.332(4) ?
N6 C50 . 1.444(4) ?
N6 C49 . 1.461(4) ?
C1 C2 . 1.499(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C7 . 1.375(5) ?
C2 C3 . 1.377(5) ?
C3 C4 . 1.376(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.333(9) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.367(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.379(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.386(4) ?
C8 C13 . 1.398(4) ?
C9 C10 . 1.379(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.372(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.371(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.397(4) ?
C12 H12 . 0.9300 ?
C14 C21 . 1.488(4) ?
C14 C15 . 1.489(4) ?
C15 C20 . 1.375(5) ?
C15 C16 . 1.394(5) ?
C16 C17 . 1.380(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.388(8) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.346(7) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.399(6) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 C23 . 1.360(4) ?
C21 C22 . 1.489(4) ?
C23 H23 . 0.9300 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C26 C27 . 1.497(4) ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C27 C28 . 1.383(4) ?
C27 C32 . 1.382(4) ?
C28 C29 . 1.382(4) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.375(5) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.369(5) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.395(4) ?
C31 H31 . 0.9300 ?
C32 H32 . 0.9300 ?
C33 C34 . 1.383(3) ?
C33 C38 . 1.403(3) ?
C34 C35 . 1.385(4) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.384(4) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.374(4) ?
C36 H36 . 0.9300 ?
C37 C38 . 1.391(3) ?
C37 H37 . 0.9300 ?
C39 C46 . 1.488(3) ?
C39 C40 . 1.490(4) ?
C40 C45 . 1.382(4) ?
C40 C41 . 1.384(4) ?
C41 C42 . 1.391(5) ?
C41 H41 . 0.9300 ?
C42 C43 . 1.346(5) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.357(5) ?
C43 H43 . 0.9300 ?
C44 C45 . 1.385(4) ?
C44 H44 . 0.9300 ?
C45 H45 . 0.9300 ?
C46 C48 . 1.360(3) ?
C46 C47 . 1.472(3) ?
C48 H48 . 0.9300 ?
C49 H49A . 0.9600 ?
C49 H49B . 0.9600 ?
C49 H49C . 0.9600 ?
C50 H50A . 0.9600 ?
C50 H50B . 0.9600 ?
C50 H50C . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C22 N1 C1 C2 . . . . -147.1(3) ?
C8 N1 C1 C2 . . . . 52.7(4) ?
N1 C1 C2 C7 . . . . 40.1(5) ?
N1 C1 C2 C3 . . . . -142.6(4) ?
C7 C2 C3 C4 . . . . 0.8(6) ?
C1 C2 C3 C4 . . . . -176.6(4) ?
C2 C3 C4 C5 . . . . -0.3(8) ?
C3 C4 C5 C6 . . . . -0.5(9) ?
C4 C5 C6 C7 . . . . 0.8(8) ?
C3 C2 C7 C6 . . . . -0.5(5) ?
C1 C2 C7 C6 . . . . 176.8(3) ?
C5 C6 C7 C2 . . . . -0.2(6) ?
C22 N1 C8 C9 . . . . -121.1(3) ?
C1 N1 C8 C9 . . . . 38.4(4) ?
C22 N1 C8 C13 . . . . 62.2(4) ?
C1 N1 C8 C13 . . . . -138.3(3) ?
C13 C8 C9 C10 . . . . 0.4(5) ?
N1 C8 C9 C10 . . . . -176.3(3) ?
C8 C9 C10 C11 . . . . 0.8(5) ?
C9 C10 C11 C12 . . . . 0.4(5) ?
C10 C11 C12 C13 . . . . -2.8(4) ?
C9 C8 C13 C12 . . . . -2.7(4) ?
N1 C8 C13 C12 . . . . 174.0(2) ?
C9 C8 C13 N2 . . . . -179.2(3) ?
N1 C8 C13 N2 . . . . -2.6(4) ?
C11 C12 C13 C8 . . . . 3.9(4) ?
C11 C12 C13 N2 . . . . -179.3(3) ?
C14 N2 C13 C8 . . . . -44.4(4) ?
C14 N2 C13 C12 . . . . 139.0(2) ?
C13 N2 C14 C21 . . . . 4.4(4) ?
C13 N2 C14 C15 . . . . 177.8(2) ?
N2 C14 C15 C20 . . . . -150.9(3) ?
C21 C14 C15 C20 . . . . 22.9(4) ?
N2 C14 C15 C16 . . . . 25.1(4) ?
C21 C14 C15 C16 . . . . -161.1(3) ?
C20 C15 C16 C17 . . . . 1.9(5) ?
C14 C15 C16 C17 . . . . -174.2(3) ?
C15 C16 C17 C18 . . . . -0.6(6) ?
C16 C17 C18 C19 . . . . -0.9(7) ?
C17 C18 C19 C20 . . . . 1.0(7) ?
C16 C15 C20 C19 . . . . -1.8(5) ?
C14 C15 C20 C19 . . . . 174.2(3) ?
C18 C19 C20 C15 . . . . 0.4(6) ?
N2 C14 C21 C23 . . . . -128.0(3) ?
C15 C14 C21 C23 . . . . 58.7(4) ?
N2 C14 C21 C22 . . . . 62.0(4) ?
C15 C14 C21 C22 . . . . -111.3(3) ?
C8 N1 C22 O1 . . . . 153.5(3) ?
C1 N1 C22 O1 . . . . -6.1(5) ?
C8 N1 C22 C21 . . . . -29.0(4) ?
C1 N1 C22 C21 . . . . 171.4(3) ?
C23 C21 C22 O1 . . . . -39.9(4) ?
C14 C21 C22 O1 . . . . 131.8(3) ?
C23 C21 C22 N1 . . . . 142.6(3) ?
C14 C21 C22 N1 . . . . -45.6(4) ?
C24 N3 C23 C21 . . . . 175.1(3) ?
C25 N3 C23 C21 . . . . 1.0(5) ?
C14 C21 C23 N3 . . . . 10.9(6) ?
C22 C21 C23 N3 . . . . -179.0(3) ?
C47 N4 C26 C27 . . . . 148.3(2) ?
C33 N4 C26 C27 . . . . -56.4(3) ?
N4 C26 C27 C28 . . . . 138.3(3) ?
N4 C26 C27 C32 . . . . -44.3(3) ?
C32 C27 C28 C29 . . . . -2.2(4) ?
C26 C27 C28 C29 . . . . 175.3(3) ?
C27 C28 C29 C30 . . . . 0.5(5) ?
C28 C29 C30 C31 . . . . 1.6(5) ?
C29 C30 C31 C32 . . . . -1.8(5) ?
C28 C27 C32 C31 . . . . 2.0(4) ?
C26 C27 C32 C31 . . . . -175.5(3) ?
C30 C31 C32 C27 . . . . 0.1(5) ?
C47 N4 C33 C34 . . . . 117.1(2) ?
C26 N4 C33 C34 . . . . -37.8(3) ?
C47 N4 C33 C38 . . . . -63.7(3) ?
C26 N4 C33 C38 . . . . 141.4(2) ?
C38 C33 C34 C35 . . . . 1.2(4) ?
N4 C33 C34 C35 . . . . -179.6(2) ?
C33 C34 C35 C36 . . . . -0.7(4) ?
C34 C35 C36 C37 . . . . -1.2(4) ?
C35 C36 C37 C38 . . . . 2.7(4) ?
C36 C37 C38 N5 . . . . -178.1(2) ?
C36 C37 C38 C33 . . . . -2.1(3) ?
C39 N5 C38 C37 . . . . -136.3(2) ?
C39 N5 C38 C33 . . . . 48.0(3) ?
C34 C33 C38 C37 . . . . 0.2(3) ?
N4 C33 C38 C37 . . . . -179.0(2) ?
C34 C33 C38 N5 . . . . 175.9(2) ?
N4 C33 C38 N5 . . . . -3.3(3) ?
C38 N5 C39 C46 . . . . -2.0(3) ?
C38 N5 C39 C40 . . . . -176.3(2) ?
N5 C39 C40 C45 . . . . 163.1(2) ?
C46 C39 C40 C45 . . . . -11.5(3) ?
N5 C39 C40 C41 . . . . -14.6(4) ?
C46 C39 C40 C41 . . . . 170.7(3) ?
C45 C40 C41 C42 . . . . 0.2(5) ?
C39 C40 C41 C42 . . . . 178.0(3) ?
C40 C41 C42 C43 . . . . 0.6(6) ?
C41 C42 C43 C44 . . . . -0.9(6) ?
C42 C43 C44 C45 . . . . 0.4(6) ?
C41 C40 C45 C44 . . . . -0.7(4) ?
C39 C40 C45 C44 . . . . -178.5(3) ?
C43 C44 C45 C40 . . . . 0.4(5) ?
N5 C39 C46 C48 . . . . 127.8(3) ?
C40 C39 C46 C48 . . . . -57.9(3) ?
N5 C39 C46 C47 . . . . -64.5(3) ?
C40 C39 C46 C47 . . . . 109.8(2) ?
C33 N4 C47 O2 . . . . -144.3(3) ?
C26 N4 C47 O2 . . . . 10.4(4) ?
C33 N4 C47 C46 . . . . 37.1(3) ?
C26 N4 C47 C46 . . . . -168.2(2) ?
C48 C46 C47 O2 . . . . 30.9(4) ?
C39 C46 C47 O2 . . . . -138.3(3) ?
C48 C46 C47 N4 . . . . -150.5(2) ?
C39 C46 C47 N4 . . . . 40.2(3) ?
C50 N6 C48 C46 . . . . -5.8(5) ?
C49 N6 C48 C46 . . . . 179.4(3) ?
C47 C46 C48 N6 . . . . 178.1(3) ?
C39 C46 C48 N6 . . . . -14.2(5) ?
