#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/15/2211582.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_2211582
loop_
_publ_author_name
'Ming Li'
'En-Tao Sun'
'Li-Rong Wen'
_publ_section_title
2-Anilino-3-benzoyl-4-(2-chlorophenyl)-7,7-dimethyl-7,8-dihydro-4H-chromen-5(6H)-one
_journal_coeditor_code           RZ2082
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5607
_journal_page_last               o5608
_journal_paper_doi               10.1107/S1600536806044266
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C30 H26 Cl N O3'
_chemical_formula_moiety         'C30 H26 Cl N O3'
_chemical_formula_sum            'C30 H26 Cl N O3'
_chemical_formula_weight         483.97
_chemical_name_systematic
;
2-Anilino-3-benzoyl-4-(2-chlorophenyl)-7,7-dimethyl-7,8-dihydro-
4H-chromen-5(6H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.956(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.982(5)
_cell_length_b                   13.768(4)
_cell_length_c                   19.018(5)
_cell_measurement_reflns_used    4318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.87
_cell_measurement_theta_min      2.20
_cell_volume                     5078(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker,  1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruck APEX-II CCD area-detector'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27044
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.266
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.329
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         8974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0450
_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)+(0.0571P)²+1.1067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                5707
_reflns_number_total             8974
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2082.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211582
_cod_database_fobs_code          2211582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl Cl1 0.16108(4) 0.48676(5) 0.33783(4) 0.0632(2) Uani d . 1
Cl Cl2 0.26123(4) 0.99927(5) 0.34510(4) 0.0704(2) Uani d . 1
O O1 0.18566(9) 0.28086(13) 0.55956(11) 0.0757(6) Uani d . 1
O O2 -0.07317(8) 0.49171(12) 0.33570(10) 0.0618(5) Uani d . 1
O O3 0.11028(8) 0.59057(10) 0.46954(8) 0.0491(4) Uani d . 1
O O4 0.34680(11) 0.79099(14) 0.56146(11) 0.0835(7) Uani d . 1
O O5 0.49362(10) 0.99592(11) 0.32865(10) 0.0628(5) Uani d . 1
O O6 0.37832(8) 1.09846(10) 0.46665(8) 0.0494(4) Uani d . 1
N N1 0.00914(9) 0.62913(13) 0.39520(10) 0.0453(5) Uani d . 1
H H1 -0.0300 0.6117 0.3682 0.054 Uiso calc R 1
N N2 0.44114(11) 1.13389(13) 0.38790(11) 0.0557(5) Uani d . 1
H H2 0.4678 1.1158 0.3609 0.067 Uiso calc R 1
C C1 0.15463(11) 0.52607(17) 0.51283(12) 0.0445(6) Uani d . 1
C C2 0.21029(12) 0.57921(18) 0.56491(13) 0.0573(7) Uani d . 1
H H2A 0.1928 0.6017 0.6054 0.069 Uiso calc R 1
H H2B 0.2237 0.6357 0.5411 0.069 Uiso calc R 1
C C3 0.27344(12) 0.51524(18) 0.59327(13) 0.0516(6) Uani d . 1
C C4 0.24839(14) 0.4188(2) 0.61678(14) 0.0710(8) Uani d . 1
H H4A 0.2876 0.3754 0.6310 0.085 Uiso calc R 1
H H4B 0.2305 0.4301 0.6592 0.085 Uiso calc R 1
C C5 0.19326(12) 0.36868(19) 0.55975(13) 0.0548(6) Uani d . 1
C C6 0.14630(11) 0.43024(16) 0.50647(11) 0.0410(5) Uani d . 1
C C7 0.08938(10) 0.38390(15) 0.44984(11) 0.0380(5) Uani d . 1
H H7 0.0661 0.3382 0.4755 0.046 Uiso calc R 1
C C8 0.11686(10) 0.32383(16) 0.39484(12) 0.0409(5) Uani d . 1
C C9 0.14557(11) 0.36239(17) 0.34220(13) 0.0489(6) Uani d . 1
C C10 0.16461(14) 0.3041(2) 0.29016(15) 0.0680(8) Uani d . 1
H H10 0.1834 0.3319 0.2547 0.082 Uiso calc R 1
C C11 0.15533(15) 0.2055(2) 0.29186(17) 0.0749(8) Uani d . 1
H H11 0.1673 0.1663 0.2570 0.090 Uiso calc R 1
C C12 0.12867(14) 0.1648(2) 0.34445(17) 0.0716(8) Uani d . 1
H H12 0.1230 0.0979 0.3457 0.086 Uiso calc R 1
C C13 0.11020(12) 0.22212(18) 0.39545(14) 0.0561(6) Uani d . 1
H H13 0.0928 0.1931 0.4315 0.067 Uiso calc R 1
C C14 0.03558(10) 0.45911(15) 0.41478(11) 0.0374(5) Uani d . 1
C C15 -0.02856(11) 0.43178(16) 0.36739(11) 0.0421(5) Uani d . 1
C C16 -0.04389(10) 0.32614(16) 0.35319(11) 0.0396(5) Uani d . 1
C C17 -0.04122(12) 0.28566(18) 0.28733(12) 0.0511(6) Uani d . 1
H H17 -0.0300 0.3241 0.2516 0.061 Uiso calc R 1
C C18 -0.05526(14) 0.18834(19) 0.27467(13) 0.0609(7) Uani d . 1
H H18 -0.0528 0.1615 0.2305 0.073 Uiso calc R 1
C C19 -0.07280(13) 0.13068(19) 0.32590(14) 0.0595(7) Uani d . 1
H H19 -0.0822 0.0651 0.3167 0.071 Uiso calc R 1
C C20 -0.07637(13) 0.17006(19) 0.39072(14) 0.0591(7) Uani d . 1
H H20 -0.0886 0.1314 0.4257 0.071 Uiso calc R 1
C C21 -0.06176(12) 0.26747(18) 0.40450(12) 0.0505(6) Uani d . 1
H H21 -0.0640 0.2937 0.4489 0.061 Uiso calc R 1
C C22 0.05076(11) 0.55663(16) 0.42556(11) 0.0393(5) Uani d . 1
C C23 0.02076(11) 0.73136(15) 0.40147(11) 0.0424(5) Uani d . 1
C C24 -0.03522(13) 0.78954(18) 0.40307(14) 0.0571(7) Uani d . 1
H H24 -0.0781 0.7617 0.4008 0.069 Uiso calc R 1
C C25 -0.02730(16) 0.88888(19) 0.40812(16) 0.0740(8) Uani d . 1
H H25 -0.0650 0.9278 0.4094 0.089 Uiso calc R 1
C C26 0.03569(17) 0.93104(19) 0.41124(15) 0.0719(8) Uani d . 1
H H26 0.0409 0.9981 0.4155 0.086 Uiso calc R 1
C C27 0.09066(14) 0.87363(19) 0.40802(13) 0.0593(7) Uani d . 1
H H27 0.1331 0.9021 0.4090 0.071 Uiso calc R 1
C C28 0.08400(12) 0.77376(17) 0.40335(12) 0.0490(6) Uani d . 1
H H28 0.1218 0.7353 0.4015 0.059 Uiso calc R 1
C C29 0.32235(15) 0.5651(2) 0.65735(15) 0.0795(9) Uani d . 1
H H29A 0.3353 0.6275 0.6425 0.119 Uiso calc R 1
H H29B 0.3628 0.5259 0.6738 0.119 Uiso calc R 1
H H29C 0.2996 0.5732 0.6960 0.119 Uiso calc R 1
C C30 0.31091(14) 0.4997(2) 0.53385(16) 0.0816(9) Uani d . 1
H H30A 0.2797 0.4725 0.4921 0.122 Uiso calc R 1
H H30B 0.3488 0.4560 0.5506 0.122 Uiso calc R 1
H H30C 0.3280 0.5608 0.5212 0.122 Uiso calc R 1
C C31 0.36073(11) 0.93959(17) 0.50701(11) 0.0432(5) Uani d . 1
C C32 0.34230(13) 0.8791(2) 0.56289(14) 0.0608(7) Uani d . 1
C C33 0.32230(18) 0.9316(2) 0.62474(16) 0.0851(10) Uani d . 1
H H33A 0.2925 0.8894 0.6445 0.102 Uiso calc R 1
H H33B 0.3637 0.9429 0.6627 0.102 Uiso calc R 1
C C34 0.28592(13) 1.02768(19) 0.60494(13) 0.0571(7) Uani d . 1
C C35 0.33010(13) 1.09086(18) 0.56797(13) 0.0573(7) Uani d . 1
H H35A 0.3028 1.1454 0.5446 0.069 Uiso calc R 1
H H35B 0.3687 1.1165 0.6043 0.069 Uiso calc R 1
C C36 0.35672(11) 1.03551(17) 0.51290(12) 0.0447(5) Uani d . 1
C C37 0.41547(11) 1.06284(16) 0.42125(12) 0.0436(5) Uani d . 1
C C38 0.42576(11) 0.96485(15) 0.41206(11) 0.0385(5) Uani d . 1
C C39 0.38778(11) 0.89118(15) 0.44835(11) 0.0403(5) Uani d . 1
H H39 0.4223 0.8437 0.4725 0.048 Uiso calc R 1
C C40 0.33230(11) 0.83403(16) 0.39465(13) 0.0458(6) Uani d . 1
C C41 0.33817(13) 0.73242(18) 0.39197(16) 0.0651(7) Uani d . 1
H H41 0.3746 0.7020 0.4242 0.078 Uiso calc R 1
C C42 0.29244(17) 0.6770(2) 0.3439(2) 0.0902(11) Uani d . 1
H H42 0.2983 0.6100 0.3434 0.108 Uiso calc R 1
C C43 0.23822(17) 0.7190(2) 0.2966(2) 0.0895(10) Uani d . 1
H H43 0.2073 0.6808 0.2635 0.107 Uiso calc R 1
C C44 0.22907(14) 0.8184(2) 0.29774(16) 0.0758(8) Uani d . 1
H H44 0.1917 0.8475 0.2660 0.091 Uiso calc R 1
C C45 0.27630(12) 0.87447(18) 0.34677(13) 0.0531(6) Uani d . 1
C C46 0.46688(11) 0.93616(16) 0.36375(12) 0.0427(5) Uani d . 1
C C47 0.47926(10) 0.83123(15) 0.35072(11) 0.0375(5) Uani d . 1
C C48 0.50989(11) 0.76785(17) 0.40613(13) 0.0474(6) Uani d . 1
H H48 0.5220 0.7897 0.4538 0.057 Uiso calc R 1
C C49 0.52237(14) 0.67245(18) 0.39050(16) 0.0625(7) Uani d . 1
H H49 0.5434 0.6308 0.4278 0.075 Uiso calc R 1
C C50 0.50423(16) 0.6387(2) 0.32098(17) 0.0712(8) Uani d . 1
H H50 0.5120 0.5741 0.3110 0.085 Uiso calc R 1
C C51 0.47461(15) 0.7005(2) 0.26624(15) 0.0685(8) Uani d . 1
H H51 0.4622 0.6779 0.2188 0.082 Uiso calc R 1
C C52 0.46300(13) 0.79621(18) 0.28084(13) 0.0540(6) Uani d . 1
H H52 0.4439 0.8379 0.2428 0.065 Uiso calc R 1
C C53 0.43014(13) 1.23568(16) 0.39120(12) 0.0452(6) Uani d . 1
C C54 0.36506(13) 1.27462(18) 0.38047(14) 0.0595(7) Uani d . 1
H H54 0.3267 1.2341 0.3719 0.071 Uiso calc R 1
C C55 0.35698(15) 1.3740(2) 0.38245(15) 0.0701(8) Uani d . 1
H H55 0.3130 1.4002 0.3758 0.084 Uiso calc R 1
C C56 0.41274(16) 1.4342(2) 0.39405(16) 0.0732(8) Uani d . 1
H H56 0.4068 1.5011 0.3950 0.088 Uiso calc R 1
C C57 0.47767(15) 1.39545(18) 0.40426(16) 0.0702(8) Uani d . 1
H H57 0.5158 1.4363 0.4122 0.084 Uiso calc R 1
C C58 0.48664(13) 1.29583(17) 0.40275(13) 0.0535(6) Uani d . 1
H H58 0.5307 1.2697 0.4095 0.064 Uiso calc R 1
C C59 0.2758(2) 1.0793(2) 0.67220(18) 0.1070(13) Uani d . 1
H H59A 0.2456 1.0417 0.6938 0.160 Uiso calc R 1
H H59B 0.2559 1.1421 0.6591 0.160 Uiso calc R 1
H H59C 0.3196 1.0866 0.7063 0.160 Uiso calc R 1
C C60 0.21569(15) 1.0131(2) 0.5532(2) 0.0930(11) Uani d . 1
H H60A 0.2214 0.9839 0.5092 0.140 Uiso calc R 1
H H60B 0.1932 1.0748 0.5424 0.140 Uiso calc R 1
H H60C 0.1881 0.9714 0.5753 0.140 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 0.0016 '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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C22 O3 C1 119.11(17) yes
C37 O6 C36 118.84(17) yes
C22 N1 C23 128.92(19) ?
C22 N1 H1 115.5 ?
C23 N1 H1 115.5 ?
C37 N2 C53 128.33(19) ?
C37 N2 H2 115.8 ?
C53 N2 H2 115.8 ?
C6 C1 O3 122.4(2) ?
C6 C1 C2 127.1(2) ?
O3 C1 C2 110.48(19) ?
C1 C2 C3 111.9(2) ?
C1 C2 H2A 109.2 ?
C3 C2 H2A 109.2 ?
C1 C2 H2B 109.2 ?
C3 C2 H2B 109.2 ?
H2A C2 H2B 107.9 ?
C30 C3 C4 110.6(2) ?
C30 C3 C2 109.5(2) ?
C4 C3 C2 107.7(2) ?
C30 C3 C29 108.8(2) ?
C4 C3 C29 110.5(2) ?
C2 C3 C29 109.7(2) ?
C5 C4 C3 114.9(2) ?
C5 C4 H4A 108.5 ?
C3 C4 H4A 108.5 ?
C5 C4 H4B 108.5 ?
C3 C4 H4B 108.5 ?
H4A C4 H4B 107.5 ?
O1 C5 C6 120.7(2) ?
O1 C5 C4 121.6(2) ?
C6 C5 C4 117.6(2) ?
C1 C6 C5 117.6(2) ?
C1 C6 C7 122.73(19) ?
C5 C6 C7 119.6(2) ?
C6 C7 C14 110.85(17) ?
C6 C7 C8 112.51(17) ?
C14 C7 C8 113.46(17) ?
C6 C7 H7 106.5 ?
C14 C7 H7 106.5 ?
C8 C7 H7 106.5 ?
C9 C8 C13 116.6(2) ?
C9 C8 C7 124.7(2) ?
C13 C8 C7 118.71(19) ?
C8 C9 C10 121.8(2) ?
C8 C9 Cl1 121.57(18) ?
C10 C9 Cl1 116.61(19) ?
C11 C10 C9 119.4(3) ?
C11 C10 H10 120.3 ?
C9 C10 H10 120.3 ?
C12 C11 C10 120.2(3) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C11 C12 C13 120.2(3) ?
C11 C12 H12 119.9 ?
C13 C12 H12 119.9 ?
C12 C13 C8 121.7(2) ?
C12 C13 H13 119.1 ?
C8 C13 H13 119.1 ?
C22 C14 C15 118.79(19) ?
C22 C14 C7 119.26(18) ?
C15 C14 C7 121.84(19) ?
O2 C15 C14 123.7(2) ?
O2 C15 C16 117.43(19) ?
C14 C15 C16 118.89(19) ?
C21 C16 C17 118.5(2) ?
C21 C16 C15 121.2(2) ?
C17 C16 C15 120.24(19) ?
C18 C17 C16 119.9(2) ?
C18 C17 H17 120.0 ?
C16 C17 H17 120.0 ?
C19 C18 C17 121.1(2) ?
C19 C18 H18 119.4 ?
C17 C18 H18 119.4 ?
C20 C19 C18 119.4(2) ?
C20 C19 H19 120.3 ?
C18 C19 H19 120.3 ?
C19 C20 C21 120.1(2) ?
C19 C20 H20 119.9 ?
C21 C20 H20 119.9 ?
C16 C21 C20 120.8(2) ?
C16 C21 H21 119.6 ?
C20 C21 H21 119.6 ?
N1 C22 O3 111.66(18) yes
N1 C22 C14 124.74(19) ?
O3 C22 C14 123.59(18) ?
C24 C23 C28 119.6(2) ?
C24 C23 N1 117.2(2) ?
C28 C23 N1 123.2(2) ?
C25 C24 C23 119.8(2) ?
C25 C24 H24 120.1 ?
C23 C24 H24 120.1 ?
C24 C25 C26 120.7(3) ?
C24 C25 H25 119.6 ?
C26 C25 H25 119.6 ?
C27 C26 C25 119.4(2) ?
C27 C26 H26 120.3 ?
C25 C26 H26 120.3 ?
C26 C27 C28 120.8(3) ?
C26 C27 H27 119.6 ?
C28 C27 H27 119.6 ?
C27 C28 C23 119.6(2) ?
C27 C28 H28 120.2 ?
C23 C28 H28 120.2 ?
C3 C29 H29A 109.5 ?
C3 C29 H29B 109.5 ?
H29A C29 H29B 109.5 ?
C3 C29 H29C 109.5 ?
H29A C29 H29C 109.5 ?
H29B C29 H29C 109.5 ?
C3 C30 H30A 109.5 ?
C3 C30 H30B 109.5 ?
H30A C30 H30B 109.5 ?
C3 C30 H30C 109.5 ?
H30A C30 H30C 109.5 ?
H30B C30 H30C 109.5 ?
C36 C31 C32 118.2(2) ?
C36 C31 C39 122.77(19) ?
C32 C31 C39 118.9(2) ?
O4 C32 C31 121.2(2) ?
O4 C32 C33 121.8(2) ?
C31 C32 C33 116.9(2) ?
C34 C33 C32 115.1(2) ?
C34 C33 H33A 108.5 ?
C32 C33 H33A 108.5 ?
C34 C33 H33B 108.5 ?
C32 C33 H33B 108.5 ?
H33A C33 H33B 107.5 ?
C33 C34 C59 110.7(2) ?
C33 C34 C60 111.0(3) ?
C59 C34 C60 108.5(2) ?
C33 C34 C35 108.4(2) ?
C59 C34 C35 109.3(2) ?
C60 C34 C35 108.9(2) ?
C36 C35 C34 112.1(2) ?
C36 C35 H35A 109.2 ?
C34 C35 H35A 109.2 ?
C36 C35 H35B 109.2 ?
C34 C35 H35B 109.2 ?
H35A C35 H35B 107.9 ?
C31 C36 O6 122.49(19) ?
C31 C36 C35 127.2(2) ?
O6 C36 C35 110.28(19) ?
N2 C37 O6 111.66(19) yes
N2 C37 C38 124.7(2) ?
O6 C37 C38 123.61(19) ?
C37 C38 C46 118.54(19) ?
C37 C38 C39 119.05(18) ?
C46 C38 C39 122.18(18) ?
C31 C39 C38 110.28(17) ?
C31 C39 C40 112.94(17) ?
C38 C39 C40 113.48(17) ?
C31 C39 H39 106.5 ?
C38 C39 H39 106.5 ?
C40 C39 H39 106.5 ?
C45 C40 C41 116.1(2) ?
C45 C40 C39 125.1(2) ?
C41 C40 C39 118.8(2) ?
C42 C41 C40 122.3(3) ?
C42 C41 H41 118.9 ?
C40 C41 H41 118.9 ?
C43 C42 C41 120.4(3) ?
C43 C42 H42 119.8 ?
C41 C42 H42 119.8 ?
C42 C43 C44 119.9(3) ?
C42 C43 H43 120.1 ?
C44 C43 H43 120.1 ?
C43 C44 C45 119.3(3) ?
C43 C44 H44 120.3 ?
C45 C44 H44 120.3 ?
C40 C45 C44 122.0(3) ?
C40 C45 Cl2 121.29(19) ?
C44 C45 Cl2 116.7(2) ?
O5 C46 C38 123.0(2) ?
O5 C46 C47 115.81(19) ?
C38 C46 C47 121.16(19) ?
C52 C47 C48 118.0(2) ?
C52 C47 C46 119.20(19) ?
C48 C47 C46 122.7(2) ?
C49 C48 C47 120.1(2) ?
C49 C48 H48 119.9 ?
C47 C48 H48 119.9 ?
C50 C49 C48 120.8(2) ?
C50 C49 H49 119.6 ?
C48 C49 H49 119.6 ?
C49 C50 C51 119.5(3) ?
C49 C50 H50 120.3 ?
C51 C50 H50 120.3 ?
C50 C51 C52 120.4(3) ?
C50 C51 H51 119.8 ?
C52 C51 H51 119.8 ?
C47 C52 C51 121.2(2) ?
C47 C52 H52 119.4 ?
C51 C52 H52 119.4 ?
C58 C53 C54 120.0(2) ?
C58 C53 N2 118.1(2) ?
C54 C53 N2 121.9(2) ?
C53 C54 C55 119.7(2) ?
C53 C54 H54 120.2 ?
C55 C54 H54 120.2 ?
C56 C55 C54 120.7(3) ?
C56 C55 H55 119.6 ?
C54 C55 H55 119.6 ?
C55 C56 C57 119.6(3) ?
C55 C56 H56 120.2 ?
C57 C56 H56 120.2 ?
C56 C57 C58 120.3(3) ?
C56 C57 H57 119.8 ?
C58 C57 H57 119.8 ?
C53 C58 C57 119.7(2) ?
C53 C58 H58 120.2 ?
C57 C58 H58 120.2 ?
C34 C59 H59A 109.5 ?
C34 C59 H59B 109.5 ?
H59A C59 H59B 109.5 ?
C34 C59 H59C 109.5 ?
H59A C59 H59C 109.5 ?
H59B C59 H59C 109.5 ?
C34 C60 H60A 109.5 ?
C34 C60 H60B 109.5 ?
H60A C60 H60B 109.5 ?
C34 C60 H60C 109.5 ?
H60A C60 H60C 109.5 ?
H60B C60 H60C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C9 1.746(2) ?
Cl2 C45 1.743(3) ?
O1 C5 1.219(3) ?
O2 C15 1.257(3) ?
O3 C22 1.361(2) yes
O3 C1 1.378(3) yes
O4 C32 1.217(3) ?
O5 C46 1.257(2) ?
O6 C37 1.359(2) yes
O6 C36 1.376(3) yes
N1 C22 1.338(3) ?
N1 C23 1.427(3) ?
N1 H1 0.8600 ?
N2 C37 1.334(3) ?
N2 C53 1.422(3) ?
N2 H2 0.8600 ?
C1 C6 1.332(3) yes
C1 C2 1.491(3) ?
C2 C3 1.527(3) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C30 1.514(4) ?
C3 C4 1.523(3) ?
C3 C29 1.529(3) ?
C4 C5 1.513(3) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C6 1.472(3) ?
C6 C7 1.507(3) ?
C7 C14 1.525(3) ?
C7 C8 1.535(3) ?
C7 H7 0.9800 ?
C8 C9 1.375(3) ?
C8 C13 1.407(3) ?
C9 C10 1.396(3) ?
C10 C11 1.371(4) ?
C10 H10 0.9300 ?
C11 C12 1.362(4) ?
C11 H11 0.9300 ?
C12 C13 1.368(4) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 C22 1.381(3) yes
C14 C15 1.428(3) ?
C15 C16 1.497(3) ?
C16 C21 1.378(3) ?
C16 C17 1.384(3) ?
C17 C18 1.378(3) ?
C17 H17 0.9300 ?
C18 C19 1.366(3) ?
C18 H18 0.9300 ?
C19 C20 1.364(3) ?
C19 H19 0.9300 ?
C20 C21 1.384(3) ?
C20 H20 0.9300 ?
C21 H21 0.9300 ?
C23 C24 1.382(3) ?
C23 C28 1.384(3) ?
C24 C25 1.378(3) ?
C24 H24 0.9300 ?
C25 C26 1.374(4) ?
C25 H25 0.9300 ?
C26 C27 1.367(4) ?
C26 H26 0.9300 ?
C27 C28 1.382(3) ?
C27 H27 0.9300 ?
C28 H28 0.9300 ?
C29 H29A 0.9600 ?
C29 H29B 0.9600 ?
C29 H29C 0.9600 ?
C30 H30A 0.9600 ?
C30 H30B 0.9600 ?
C30 H30C 0.9600 ?
C31 C36 1.329(3) yes
C31 C32 1.465(3) ?
C31 C39 1.507(3) ?
C32 C33 1.514(4) ?
C33 C34 1.513(4) ?
C33 H33A 0.9700 ?
C33 H33B 0.9700 ?
C34 C59 1.519(4) ?
C34 C60 1.520(4) ?
C34 C35 1.526(3) ?
C35 C36 1.493(3) ?
C35 H35A 0.9700 ?
C35 H35B 0.9700 ?
C37 C38 1.382(3) yes
C38 C46 1.428(3) ?
C38 C39 1.528(3) ?
C39 C40 1.531(3) ?
C39 H39 0.9800 ?
C40 C45 1.378(3) ?
C40 C41 1.406(3) ?
C41 C42 1.361(4) ?
C41 H41 0.9300 ?
C42 C43 1.359(4) ?
C42 H42 0.9300 ?
C43 C44 1.382(4) ?
C43 H43 0.9300 ?
C44 C45 1.390(4) ?
C44 H44 0.9300 ?
C46 C47 1.496(3) ?
C47 C52 1.377(3) ?
C47 C48 1.391(3) ?
C48 C49 1.383(3) ?
C48 H48 0.9300 ?
C49 C50 1.365(4) ?
C49 H49 0.9300 ?
C50 C51 1.364(4) ?
C50 H50 0.9300 ?
C51 C52 1.378(3) ?
C51 H51 0.9300 ?
C52 H52 0.9300 ?
C53 C58 1.374(3) ?
C53 C54 1.376(3) ?
C54 C55 1.380(3) ?
C54 H54 0.9300 ?
C55 C56 1.363(4) ?
C55 H55 0.9300 ?
C56 C57 1.373(4) ?
C56 H56 0.9300 ?
C57 C58 1.384(3) ?
C57 H57 0.9300 ?
C58 H58 0.9300 ?
C59 H59A 0.9600 ?
C59 H59B 0.9600 ?
C59 H59C 0.9600 ?
C60 H60A 0.9600 ?
C60 H60B 0.9600 ?
C60 H60C 0.9600 ?
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
C21 H21 O3 3_566 0.93 2.55 3.409(3) 154.2
C24 H24 O1 3_566 0.93 2.51 3.393(3) 158.0
N1 H1 O2 . 0.86 1.90 2.582(2) 135.6
N2 H2 O5 . 0.86 1.88 2.559(2) 135.1
C28 H28 O3 . 0.93 2.42 2.811(3) 105.5
C58 H58 O4 3_676 0.93 2.52 3.446(3) 174.5
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_publ_flag
C22 O3 C1 C6 9.2(3) ?
C22 O3 C1 C2 -170.82(19) ?
C6 C1 C2 C3 21.3(3) ?
O3 C1 C2 C3 -158.70(19) ?
C1 C2 C3 C30 72.4(3) ?
C1 C2 C3 C4 -48.0(3) ?
C1 C2 C3 C29 -168.3(2) ?
C30 C3 C4 C5 -66.2(3) ?
C2 C3 C4 C5 53.4(3) ?
C29 C3 C4 C5 173.2(2) ?
C3 C4 C5 O1 153.7(3) ?
C3 C4 C5 C6 -29.6(3) ?
O3 C1 C6 C5 -174.8(2) ?
C2 C1 C6 C5 5.3(4) ?
O3 C1 C6 C7 2.3(3) ?
C2 C1 C6 C7 -177.7(2) ?
O1 C5 C6 C1 175.5(2) ?
C4 C5 C6 C1 -1.2(3) ?
O1 C5 C6 C7 -1.6(4) ?
C4 C5 C6 C7 -178.4(2) ?
C1 C6 C7 C14 -13.0(3) ?
C5 C6 C7 C14 163.98(19) ?
C1 C6 C7 C8 115.2(2) ?
C5 C6 C7 C8 -67.8(3) ?
C6 C7 C8 C9 -71.9(3) ?
C14 C7 C8 C9 55.0(3) ?
C6 C7 C8 C13 110.8(2) ?
C14 C7 C8 C13 -122.3(2) ?
C13 C8 C9 C10 2.5(3) ?
C7 C8 C9 C10 -174.8(2) ?
C13 C8 C9 Cl1 -176.65(17) ?
C7 C8 C9 Cl1 6.0(3) ?
C8 C9 C10 C11 -0.8(4) ?
Cl1 C9 C10 C11 178.4(2) ?
C9 C10 C11 C12 -0.9(4) ?
C10 C11 C12 C13 0.8(5) ?
C11 C12 C13 C8 1.1(4) ?
C9 C8 C13 C12 -2.6(3) ?
C7 C8 C13 C12 174.9(2) ?
C6 C7 C14 C22 13.5(3) ?
C8 C7 C14 C22 -114.2(2) ?
C6 C7 C14 C15 -170.45(18) ?
C8 C7 C14 C15 61.8(3) ?
C22 C14 C15 O2 -1.6(3) ?
C7 C14 C15 O2 -177.6(2) ?
C22 C14 C15 C16 177.49(19) ?
C7 C14 C15 C16 1.4(3) ?
O2 C15 C16 C21 -106.1(2) ?
C14 C15 C16 C21 74.8(3) ?
O2 C15 C16 C17 73.0(3) ?
C14 C15 C16 C17 -106.1(2) ?
C21 C16 C17 C18 -1.0(3) ?
C15 C16 C17 C18 179.9(2) ?
C16 C17 C18 C19 0.9(4) ?
C17 C18 C19 C20 -0.1(4) ?
C18 C19 C20 C21 -0.5(4) ?
C17 C16 C21 C20 0.3(3) ?
C15 C16 C21 C20 179.5(2) ?
C19 C20 C21 C16 0.4(4) ?
C23 N1 C22 O3 2.4(3) yes
C23 N1 C22 C14 -178.3(2) ?
C1 O3 C22 N1 171.06(18) ?
C1 O3 C22 C14 -8.3(3) ?
C15 C14 C22 N1 0.7(3) ?
C7 C14 C22 N1 176.91(19) ?
C15 C14 C22 O3 179.97(19) ?
C7 C14 C22 O3 -3.9(3) ?
C22 N1 C23 C24 -143.7(2) ?
C22 N1 C23 C28 38.6(3) ?
C28 C23 C24 C25 -1.4(4) ?
N1 C23 C24 C25 -179.2(2) ?
C23 C24 C25 C26 0.3(4) ?
C24 C25 C26 C27 1.1(5) ?
C25 C26 C27 C28 -1.5(4) ?
C26 C27 C28 C23 0.4(4) ?
C24 C23 C28 C27 1.1(3) ?
N1 C23 C28 C27 178.7(2) ?
C36 C31 C32 O4 -177.9(3) ?
C39 C31 C32 O4 -1.9(4) ?
C36 C31 C32 C33 -2.0(4) ?
C39 C31 C32 C33 174.0(2) ?
O4 C32 C33 C34 -151.4(3) ?
C31 C32 C33 C34 32.7(4) ?
C32 C33 C34 C59 -173.4(3) ?
C32 C33 C34 C60 66.1(3) ?
C32 C33 C34 C35 -53.5(4) ?
C33 C34 C35 C36 45.0(3) ?
C59 C34 C35 C36 165.7(2) ?
C60 C34 C35 C36 -75.9(3) ?
C32 C31 C36 O6 174.5(2) ?
C39 C31 C36 O6 -1.4(3) ?
C32 C31 C36 C35 -5.0(4) ?
C39 C31 C36 C35 179.2(2) ?
C37 O6 C36 C31 -11.3(3) ?
C37 O6 C36 C35 168.24(19) ?
C34 C35 C36 C31 -18.1(4) ?
C34 C35 C36 O6 162.4(2) ?
C53 N2 C37 O6 -4.5(3) yes
C53 N2 C37 C38 176.3(2) ?
C36 O6 C37 N2 -170.73(19) ?
C36 O6 C37 C38 8.4(3) ?
N2 C37 C38 C46 0.2(3) ?
O6 C37 C38 C46 -178.9(2) ?
N2 C37 C38 C39 -174.4(2) ?
O6 C37 C38 C39 6.6(3) ?
C36 C31 C39 C38 14.8(3) ?
C32 C31 C39 C38 -161.0(2) ?
C36 C31 C39 C40 -113.4(2) ?
C32 C31 C39 C40 70.8(3) ?
C37 C38 C39 C31 -16.9(3) ?
C46 C38 C39 C31 168.71(19) ?
C37 C38 C39 C40 110.9(2) ?
C46 C38 C39 C40 -63.4(3) ?
C31 C39 C40 C45 67.2(3) ?
C38 C39 C40 C45 -59.3(3) ?
C31 C39 C40 C41 -113.9(2) ?
C38 C39 C40 C41 119.6(2) ?
C45 C40 C41 C42 1.6(4) ?
C39 C40 C41 C42 -177.5(2) ?
C40 C41 C42 C43 -0.7(5) ?
C41 C42 C43 C44 -0.6(5) ?
C42 C43 C44 C45 1.0(5) ?
C41 C40 C45 C44 -1.2(4) ?
C39 C40 C45 C44 177.8(2) ?
C41 C40 C45 Cl2 178.65(18) ?
C39 C40 C45 Cl2 -2.4(3) ?
C43 C44 C45 C40 -0.1(4) ?
C43 C44 C45 Cl2 -179.9(2) ?
C37 C38 C46 O5 -0.7(3) ?
C39 C38 C46 O5 173.7(2) ?
C37 C38 C46 C47 -179.2(2) ?
C39 C38 C46 C47 -4.8(3) ?
O5 C46 C47 C52 -53.8(3) ?
C38 C46 C47 C52 124.9(2) ?
O5 C46 C47 C48 122.9(2) ?
C38 C46 C47 C48 -58.4(3) ?
C52 C47 C48 C49 -0.8(3) ?
C46 C47 C48 C49 -177.6(2) ?
C47 C48 C49 C50 -0.8(4) ?
C48 C49 C50 C51 1.2(4) ?
C49 C50 C51 C52 0.0(4) ?
C48 C47 C52 C51 2.0(3) ?
C46 C47 C52 C51 178.9(2) ?
C50 C51 C52 C47 -1.6(4) ?
C37 N2 C53 C58 132.7(3) ?
C37 N2 C53 C54 -49.9(4) ?
C58 C53 C54 C55 -1.0(4) ?
N2 C53 C54 C55 -178.4(2) ?
C53 C54 C55 C56 0.8(4) ?
C54 C55 C56 C57 -0.3(5) ?
C55 C56 C57 C58 0.1(5) ?
C54 C53 C58 C57 0.7(4) ?
N2 C53 C58 C57 178.2(2) ?
C56 C57 C58 C53 -0.2(4) ?
