#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/55/2225540.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_2225540
loop_
_publ_author_name
'Gunasekaran, B.'
'Kathiravan, S.'
'Raghunathan, R.'
'Manivannan, V.'
_publ_section_title
;
 Methyl
 4-(4-chlorophenyl)-1,2,3,3a,4,4a,5,12c-octahydrobenzo[f]chromeno[3,4-b]pyrrolizine-4a-carboxylate
;
_journal_coeditor_code           GK2258
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o810
_journal_page_last               o811
_journal_paper_doi               10.1107/S1600536810007804
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H24 Cl N O3'
_chemical_formula_moiety         'C26 H24 Cl N O3'
_chemical_formula_sum            'C26 H24 Cl N O3'
_chemical_formula_weight         433.91
_chemical_name_systematic
;
Methyl 4-(4-chlorophenyl)-1,2,3,3a,4,4a,5,12c-
octahydrobenzo[f]chromeno[3,4-b]pyrrolizine-4a-carboxylate
;
_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                 102.756(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.3214(9)
_cell_length_b                   10.8122(5)
_cell_length_c                   18.5008(8)
_cell_measurement_reflns_used    6164
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.46
_cell_volume                     4354.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40734
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         0.94
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.551
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         10819
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0823P)²+1.6776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.2006
_reflns_number_gt                5771
_reflns_number_total             10819
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2258.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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225540
_cod_database_fobs_code          2225540
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.07636(12) 0.0026(3) 0.73870(14) 0.0533(6) Uani d . 1 . .
H H1 -0.0470 0.0651 0.7470 0.064 Uiso calc R 1 . .
C C2 -0.12729(14) 0.0129(3) 0.76812(16) 0.0641(8) Uani d . 1 . .
H H2 -0.1322 0.0823 0.7960 0.077 Uiso calc R 1 . .
C C3 -0.17171(14) -0.0793(3) 0.75678(17) 0.0694(9) Uani d . 1 . .
H H3 -0.2068 -0.0701 0.7756 0.083 Uiso calc R 1 . .
C C4 -0.16401(13) -0.1825(3) 0.71836(16) 0.0631(8) Uani d . 1 . .
H H4 -0.1936 -0.2445 0.7119 0.076 Uiso calc R 1 . .
C C5 -0.11179(12) -0.1972(3) 0.68793(14) 0.0506(6) Uani d . 1 . .
C C6 -0.10198(13) -0.3072(3) 0.65035(15) 0.0581(7) Uani d . 1 . .
H H6 -0.1306 -0.3709 0.6452 0.070 Uiso calc R 1 . .
C C7 -0.05150(12) -0.3204(2) 0.62199(15) 0.0539(6) Uani d . 1 . .
H H7 -0.0449 -0.3940 0.5990 0.065 Uiso calc R 1 . .
C C8 -0.00902(11) -0.2231(2) 0.62717(13) 0.0455(6) Uani d . 1 . .
C C9 -0.01553(11) -0.1132(2) 0.66223(12) 0.0431(5) Uani d . 1 . .
C C10 -0.06751(11) -0.1020(2) 0.69571(12) 0.0450(6) Uani d . 1 . .
C C11 0.03076(10) -0.0100(2) 0.66425(13) 0.0425(5) Uani d . 1 . .
H H11 0.0413 0.0252 0.7143 0.051 Uiso calc R 1 . .
C C12 0.08965(11) -0.0557(2) 0.64277(13) 0.0447(6) Uani d . 1 . .
C C13 0.07239(11) -0.1440(2) 0.57766(13) 0.0474(6) Uani d . 1 . .
H H13A 0.0472 -0.1008 0.5359 0.057 Uiso calc R 1 . .
H H13B 0.1094 -0.1717 0.5632 0.057 Uiso calc R 1 . .
C C14 -0.02061(14) 0.1973(2) 0.63721(16) 0.0601(7) Uani d . 1 . .
H H14A -0.0045 0.2097 0.6899 0.072 Uiso calc R 1 . .
H H14B -0.0648 0.1867 0.6283 0.072 Uiso calc R 1 . .
C C15 -0.00443(14) 0.3051(3) 0.59322(16) 0.0606(7) Uani d . 1 . .
H H15A -0.0323 0.3103 0.5450 0.073 Uiso calc R 1 . .
H H15B -0.0056 0.3825 0.6194 0.073 Uiso calc R 1 . .
C C16 0.05997(14) 0.2756(3) 0.58591(17) 0.0636(8) Uani d . 1 . .
H H16A 0.0900 0.3021 0.6295 0.076 Uiso calc R 1 . .
H H16B 0.0691 0.3150 0.5425 0.076 Uiso calc R 1 . .
C C17 0.05954(11) 0.1360(2) 0.57842(15) 0.0516(6) Uani d . 1 . .
H H17 0.0511 0.1147 0.5257 0.062 Uiso calc R 1 . .
C C18 0.11705(11) 0.0657(3) 0.61847(14) 0.0507(6) Uani d . 1 . .
H H18 0.1349 0.1120 0.6636 0.061 Uiso calc R 1 . .
C C19 0.16677(12) 0.0508(3) 0.57547(15) 0.0538(6) Uani d . 1 . .
C C20 0.15403(14) 0.0320(3) 0.49928(16) 0.0648(8) Uani d . 1 . .
H H20 0.1133 0.0294 0.4732 0.078 Uiso calc R 1 . .
C C21 0.20021(16) 0.0171(3) 0.46145(19) 0.0745(9) Uani d . 1 . .
H H21 0.1906 0.0033 0.4106 0.089 Uiso calc R 1 . .
C C22 0.25994(16) 0.0226(3) 0.4986(2) 0.0781(9) Uani d U 1 . .
C C23 0.27455(15) 0.0397(4) 0.5730(2) 0.0866(10) Uani d U 1 . .
H H23 0.3155 0.0417 0.5982 0.104 Uiso calc R 1 . .
C C24 0.22811(13) 0.0542(3) 0.61148(19) 0.0744(9) Uani d . 1 . .
H H24 0.2385 0.0665 0.6625 0.089 Uiso calc R 1 . .
C C25 0.13534(11) -0.1199(3) 0.70353(14) 0.0497(6) Uani d . 1 . .
C C26 0.17634(18) -0.1413(4) 0.83147(17) 0.0989(13) Uani d . 1 . .
H H26A 0.1757 -0.2298 0.8267 0.148 Uiso calc R 1 . .
H H26B 0.1669 -0.1189 0.8779 0.148 Uiso calc R 1 . .
H H26C 0.2164 -0.1108 0.8297 0.148 Uiso calc R 1 . .
C C27 0.27507(12) -0.1797(3) 1.01938(14) 0.0554(7) Uani d . 1 . .
H H27 0.2977 -0.2516 1.0183 0.067 Uiso calc R 1 . .
C C28 0.22600(14) -0.1821(3) 1.05207(16) 0.0714(9) Uani d . 1 . .
H H28 0.2159 -0.2551 1.0731 0.086 Uiso calc R 1 . .
C C29 0.19090(15) -0.0768(4) 1.05429(18) 0.0810(10) Uani d . 1 . .
H H29 0.1575 -0.0793 1.0767 0.097 Uiso calc R 1 . .
C C30 0.20549(14) 0.0296(4) 1.02362(17) 0.0747(9) Uani d . 1 . .
H H30 0.1822 0.1002 1.0259 0.090 Uiso calc R 1 . .
C C31 0.25532(12) 0.0358(3) 0.98824(14) 0.0561(7) Uani d . 1 . .
C C32 0.26886(14) 0.1441(3) 0.95261(17) 0.0656(8) Uani d . 1 . .
H H32 0.2454 0.2148 0.9538 0.079 Uiso calc R 1 . .
C C33 0.31533(14) 0.1470(3) 0.91679(17) 0.0636(7) Uani d . 1 . .
H H33 0.3230 0.2187 0.8925 0.076 Uiso calc R 1 . .
C C34 0.35220(12) 0.0419(3) 0.91605(14) 0.0513(6) Uani d . 1 . .
C C35 0.34343(11) -0.0648(2) 0.95212(13) 0.0454(6) Uani d . 1 . .
C C36 0.29225(11) -0.0707(2) 0.98716(13) 0.0464(6) Uani d . 1 . .
C C37 0.38691(12) -0.1712(2) 0.95372(14) 0.0503(6) Uani d . 1 . .
H H37 0.3648 -0.2498 0.9517 0.060 Uiso calc R 1 . .
C C38 0.42144(11) -0.1641(3) 0.89047(14) 0.0515(6) Uani d . 1 C .
C C39 0.44475(12) -0.0338(3) 0.88659(15) 0.0552(7) Uani d . 1 . .
H H39A 0.4746 -0.0155 0.9320 0.066 Uiso calc R 1 . .
H H39B 0.4655 -0.0279 0.8458 0.066 Uiso calc R 1 . .
C C40 0.42860(16) -0.2218(4) 1.08863(17) 0.0810(10) Uani d . 1 . .
H H40A 0.3924 -0.2741 1.0787 0.097 Uiso calc R 1 A 1
H H40B 0.4230 -0.1575 1.1231 0.097 Uiso calc R 1 A 1
C C42 0.5073(2) -0.3374(4) 1.05483(19) 0.0912(12) Uani d . 1 . .
H H42A 0.4861 -0.4114 1.0331 0.109 Uiso calc R 1 B 1
H H42B 0.5512 -0.3533 1.0676 0.109 Uiso calc R 1 B 1
C C43 0.49248(15) -0.2293(3) 1.00385(17) 0.0700(8) Uani d . 1 C .
H H43 0.5272 -0.1716 1.0143 0.084 Uiso calc R 1 . .
C C44 0.47562(13) -0.2556(3) 0.91870(16) 0.0611(7) Uani d . 1 . .
H H44 0.4591 -0.3398 0.9117 0.073 Uiso calc R 1 C .
C C45 0.52890(12) -0.2479(3) 0.88104(14) 0.0521(6) Uani d . 1 C .
C C46 0.57228(13) -0.1541(3) 0.89731(17) 0.0672(8) Uani d . 1 . .
H H46 0.5694 -0.0966 0.9338 0.081 Uiso calc R 1 C .
C C47 0.61934(13) -0.1444(3) 0.86064(18) 0.0711(9) Uani d . 1 C .
H H47 0.6477 -0.0804 0.8717 0.085 Uiso calc R 1 . .
C C48 0.62386(13) -0.2299(3) 0.80779(17) 0.0690(8) Uani d . 1 . .
C C49 0.58322(14) -0.3254(3) 0.79190(17) 0.0719(9) Uani d . 1 C .
H H49 0.5877 -0.3851 0.7572 0.086 Uiso calc R 1 . .
C C50 0.53543(13) -0.3326(3) 0.82786(16) 0.0633(8) Uani d . 1 . .
H H50 0.5069 -0.3962 0.8159 0.076 Uiso calc R 1 C .
C C51 0.38363(13) -0.2008(3) 0.81484(17) 0.0628(7) Uani d . 1 . .
C C52 0.3130(2) -0.3414(5) 0.7477(2) 0.1147(15) Uani d . 1 . .
H H52A 0.2933 -0.2728 0.7191 0.172 Uiso calc R 1 C .
H H52B 0.2824 -0.3982 0.7568 0.172 Uiso calc R 1 . .
H H52C 0.3394 -0.3827 0.7210 0.172 Uiso calc R 1 . .
N N1 0.00836(9) 0.08961(18) 0.61034(11) 0.0453(5) Uani d . 1 . .
N N2 0.43864(10) -0.1676(2) 1.02015(12) 0.0621(6) Uani d . 1 C .
O O1 0.03955(8) -0.24894(16) 0.59566(10) 0.0536(4) Uani d . 1 . .
O O2 0.17254(10) -0.1925(2) 0.69264(11) 0.0794(7) Uani d . 1 . .
O O3 0.13110(10) -0.0879(2) 0.77133(10) 0.0796(7) Uani d . 1 . .
O O4 0.39666(9) 0.05623(18) 0.87646(11) 0.0625(5) Uani d . 1 . .
O O5 0.38716(15) -0.1522(3) 0.75852(13) 0.1160(10) Uani d . 1 C .
O O6 0.34906(11) -0.2967(2) 0.81782(12) 0.0883(7) Uani d . 1 C .
Cl Cl1 0.31782(5) 0.00823(10) 0.44984(8) 0.1211(5) Uani d . 1 . .
Cl Cl2 0.68286(5) -0.21687(13) 0.76101(7) 0.1163(4) Uani d . 1 C .
C C41 0.4847(5) -0.2963(9) 1.1198(4) 0.077(2) Uani d P 0.69(2) C 1
H H41A 0.5153 -0.2462 1.1523 0.092 Uiso calc PR 0.69(2) C 1
H H41B 0.4746 -0.3666 1.1474 0.092 Uiso calc PR 0.69(2) C 1
C C41A 0.4516(12) -0.3365(15) 1.0949(12) 0.080(5) Uani d P 0.31(2) C 2
H H41C 0.4206 -0.3954 1.0717 0.096 Uiso calc PR 0.31(2) C 2
H H41D 0.4656 -0.3585 1.1467 0.096 Uiso calc PR 0.31(2) C 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 121.2(3) ?
C2 C1 H1 . . 119.4 ?
C10 C1 H1 . . 119.4 ?
C1 C2 C3 . . 120.6(3) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 120.1(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 121.0(3) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C4 C5 C10 . . 119.9(3) ?
C4 C5 C6 . . 121.4(3) ?
C10 C5 C6 . . 118.7(2) ?
C7 C6 C5 . . 120.8(3) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 120.1(3) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
O1 C8 C9 . . 123.6(2) ?
O1 C8 C7 . . 113.8(2) ?
C9 C8 C7 . . 122.6(2) ?
C8 C9 C10 . . 117.1(2) ?
C8 C9 C11 . . 120.3(2) ?
C10 C9 C11 . . 122.6(2) ?
C5 C10 C1 . . 117.2(2) ?
C5 C10 C9 . . 120.6(2) ?
C1 C10 C9 . . 122.3(2) ?
N1 C11 C9 . . 113.13(18) ?
N1 C11 C12 . . 103.94(18) ?
C9 C11 C12 . . 112.0(2) ?
N1 C11 H11 . . 109.2 ?
C9 C11 H11 . . 109.2 ?
C12 C11 H11 . . 109.2 ?
C25 C12 C13 . . 108.2(2) ?
C25 C12 C11 . . 115.5(2) ?
C13 C12 C11 . . 109.01(19) ?
C25 C12 C18 . . 111.1(2) ?
C13 C12 C18 . . 110.4(2) ?
C11 C12 C18 . . 102.53(19) ?
O1 C13 C12 . . 111.57(19) ?
O1 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
O1 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
N1 C14 C15 . . 104.7(2) ?
N1 C14 H14A . . 110.8 ?
C15 C14 H14A . . 110.8 ?
N1 C14 H14B . . 110.8 ?
C15 C14 H14B . . 110.8 ?
H14A C14 H14B . . 108.9 ?
C16 C15 C14 . . 103.4(2) ?
C16 C15 H15A . . 111.1 ?
C14 C15 H15A . . 111.1 ?
C16 C15 H15B . . 111.1 ?
C14 C15 H15B . . 111.1 ?
H15A C15 H15B . . 109.1 ?
C15 C16 C17 . . 103.4(2) ?
C15 C16 H16A . . 111.1 ?
C17 C16 H16A . . 111.1 ?
C15 C16 H16B . . 111.1 ?
C17 C16 H16B . . 111.1 ?
H16A C16 H16B . . 109.0 ?
N1 C17 C16 . . 106.9(2) ?
N1 C17 C18 . . 106.0(2) ?
C16 C17 C18 . . 117.5(2) ?
N1 C17 H17 . . 108.7 ?
C16 C17 H17 . . 108.7 ?
C18 C17 H17 . . 108.7 ?
C19 C18 C17 . . 115.6(2) ?
C19 C18 C12 . . 116.4(2) ?
C17 C18 C12 . . 102.54(19) ?
C19 C18 H18 . . 107.3 ?
C17 C18 H18 . . 107.3 ?
C12 C18 H18 . . 107.3 ?
C24 C19 C20 . . 116.8(3) ?
C24 C19 C18 . . 120.5(3) ?
C20 C19 C18 . . 122.7(2) ?
C21 C20 C19 . . 121.6(3) ?
C21 C20 H20 . . 119.2 ?
C19 C20 H20 . . 119.2 ?
C22 C21 C20 . . 119.9(3) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C23 C22 C21 . . 120.6(3) ?
C23 C22 Cl1 . . 120.0(3) ?
C21 C22 Cl1 . . 119.4(3) ?
C22 C23 C24 . . 119.7(3) ?
C22 C23 H23 . . 120.1 ?
C24 C23 H23 . . 120.1 ?
C19 C24 C23 . . 121.4(3) ?
C19 C24 H24 . . 119.3 ?
C23 C24 H24 . . 119.3 ?
O2 C25 O3 . . 122.1(2) ?
O2 C25 C12 . . 124.0(2) ?
O3 C25 C12 . . 114.0(2) ?
O3 C26 H26A . . 109.5 ?
O3 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
O3 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C28 C27 C36 . . 121.5(3) ?
C28 C27 H27 . . 119.2 ?
C36 C27 H27 . . 119.2 ?
C27 C28 C29 . . 120.8(3) ?
C27 C28 H28 . . 119.6 ?
C29 C28 H28 . . 119.6 ?
C30 C29 C28 . . 119.7(3) ?
C30 C29 H29 . . 120.2 ?
C28 C29 H29 . . 120.2 ?
C29 C30 C31 . . 121.4(3) ?
C29 C30 H30 . . 119.3 ?
C31 C30 H30 . . 119.3 ?
C32 C31 C30 . . 121.9(3) ?
C32 C31 C36 . . 118.9(2) ?
C30 C31 C36 . . 119.2(3) ?
C33 C32 C31 . . 121.1(3) ?
C33 C32 H32 . . 119.4 ?
C31 C32 H32 . . 119.4 ?
C32 C33 C34 . . 120.1(3) ?
C32 C33 H33 . . 120.0 ?
C34 C33 H33 . . 120.0 ?
O4 C34 C35 . . 123.8(2) ?
O4 C34 C33 . . 114.2(2) ?
C35 C34 C33 . . 122.0(2) ?
C34 C35 C36 . . 118.2(2) ?
C34 C35 C37 . . 119.6(2) ?
C36 C35 C37 . . 122.2(2) ?
C27 C36 C31 . . 117.3(2) ?
C27 C36 C35 . . 123.1(2) ?
C31 C36 C35 . . 119.6(2) ?
N2 C37 C35 . . 112.1(2) ?
N2 C37 C38 . . 101.48(19) ?
C35 C37 C38 . . 112.2(2) ?
N2 C37 H37 . . 110.3 ?
C35 C37 H37 . . 110.3 ?
C38 C37 H37 . . 110.3 ?
C39 C38 C51 . . 109.1(2) ?
C39 C38 C37 . . 108.6(2) ?
C51 C38 C37 . . 114.7(2) ?
C39 C38 C44 . . 111.0(2) ?
C51 C38 C44 . . 112.0(2) ?
C37 C38 C44 . . 101.3(2) ?
O4 C39 C38 . . 112.6(2) ?
O4 C39 H39A . . 109.1 ?
C38 C39 H39A . . 109.1 ?
O4 C39 H39B . . 109.1 ?
C38 C39 H39B . . 109.1 ?
H39A C39 H39B . . 107.8 ?
C41A C40 N2 . . 108.5(6) ?
C41A C40 C41 . . 36.2(9) ?
N2 C40 C41 . . 106.0(3) ?
C41A C40 H40A . . 76.4 ?
N2 C40 H40A . . 110.5 ?
C41 C40 H40A . . 110.5 ?
C41A C40 H40B . . 135.2 ?
N2 C40 H40B . . 110.5 ?
C41 C40 H40B . . 110.5 ?
H40A C40 H40B . . 108.7 ?
C41 C42 C43 . . 102.2(3) ?
C41 C42 C41A . . 33.7(6) ?
C43 C42 C41A . . 101.7(5) ?
C41 C42 H42A . . 111.3 ?
C43 C42 H42A . . 111.3 ?
C41A C42 H42A . . 80.7 ?
C41 C42 H42B . . 111.3 ?
C43 C42 H42B . . 111.3 ?
C41A C42 H42B . . 137.9 ?
H42A C42 H42B . . 109.2 ?
N2 C43 C42 . . 107.7(3) ?
N2 C43 C44 . . 105.3(2) ?
C42 C43 C44 . . 117.7(3) ?
N2 C43 H43 . . 108.6 ?
C42 C43 H43 . . 108.6 ?
C44 C43 H43 . . 108.6 ?
C45 C44 C38 . . 116.3(2) ?
C45 C44 C43 . . 114.6(2) ?
C38 C44 C43 . . 102.6(2) ?
C45 C44 H44 . . 107.6 ?
C38 C44 H44 . . 107.6 ?
C43 C44 H44 . . 107.6 ?
C50 C45 C46 . . 117.5(2) ?
C50 C45 C44 . . 120.9(3) ?
C46 C45 C44 . . 121.6(2) ?
C47 C46 C45 . . 121.4(3) ?
C47 C46 H46 . . 119.3 ?
C45 C46 H46 . . 119.3 ?
C48 C47 C46 . . 119.2(3) ?
C48 C47 H47 . . 120.4 ?
C46 C47 H47 . . 120.4 ?
C49 C48 C47 . . 121.1(3) ?
C49 C48 Cl2 . . 119.8(2) ?
C47 C48 Cl2 . . 119.2(3) ?
C48 C49 C50 . . 119.2(3) ?
C48 C49 H49 . . 120.4 ?
C50 C49 H49 . . 120.4 ?
C45 C50 C49 . . 121.6(3) ?
C45 C50 H50 . . 119.2 ?
C49 C50 H50 . . 119.2 ?
O5 C51 O6 . . 123.1(3) ?
O5 C51 C38 . . 124.3(3) ?
O6 C51 C38 . . 112.5(3) ?
O6 C52 H52A . . 109.5 ?
O6 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
O6 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
C14 N1 C11 . . 117.21(19) ?
C14 N1 C17 . . 107.5(2) ?
C11 N1 C17 . . 109.84(18) ?
C40 N2 C43 . . 106.7(2) ?
C40 N2 C37 . . 117.8(2) ?
C43 N2 C37 . . 109.9(2) ?
C8 O1 C13 . . 115.63(19) ?
C25 O3 C26 . . 116.1(2) ?
C34 O4 C39 . . 117.8(2) ?
C51 O6 C52 . . 116.4(3) ?
C42 C41 C40 . . 105.0(5) ?
C42 C41 H41A . . 110.8 ?
C40 C41 H41A . . 110.8 ?
C42 C41 H41B . . 110.8 ?
C40 C41 H41B . . 110.8 ?
H41A C41 H41B . . 108.8 ?
C40 C41A C42 . . 107.0(10) ?
C40 C41A H41C . . 110.3 ?
C42 C41A H41C . . 110.3 ?
C40 C41A H41D . . 110.3 ?
C42 C41A H41D . . 110.3 ?
H41C C41A H41D . . 108.6 ?
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
C1 C2 . 1.369(4) ?
C1 C10 . 1.421(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.389(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.354(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.411(4) ?
C4 H4 . 0.9300 ?
C5 C10 . 1.412(4) ?
C5 C6 . 1.418(4) ?
C6 C7 . 1.351(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.405(4) ?
C7 H7 . 0.9300 ?
C8 O1 . 1.368(3) ?
C8 C9 . 1.376(3) ?
C9 C10 . 1.436(3) ?
C9 C11 . 1.516(3) ?
C11 N1 . 1.478(3) ?
C11 C12 . 1.536(3) ?
C11 H11 . 0.9800 ?
C12 C25 . 1.510(3) ?
C12 C13 . 1.519(3) ?
C12 C18 . 1.555(4) ?
C13 O1 . 1.429(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 N1 . 1.471(3) ?
C14 C15 . 1.510(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.507(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.516(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 N1 . 1.484(3) ?
C17 C18 . 1.535(4) ?
C17 H17 . 0.9800 ?
C18 C19 . 1.510(3) ?
C18 H18 . 0.9800 ?
C19 C24 . 1.385(4) ?
C19 C20 . 1.390(4) ?
C20 C21 . 1.377(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.360(5) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.355(5) ?
C22 Cl1 . 1.739(3) ?
C23 C24 . 1.390(4) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
C25 O2 . 1.192(3) ?
C25 O3 . 1.325(3) ?
C26 O3 . 1.448(4) ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C27 C28 . 1.363(4) ?
C27 C36 . 1.411(4) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.388(5) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.354(5) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.411(4) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.409(4) ?
C31 C36 . 1.419(4) ?
C32 C33 . 1.349(4) ?
C32 H32 . 0.9300 ?
C33 C34 . 1.405(4) ?
C33 H33 . 0.9300 ?
C34 O4 . 1.366(3) ?
C34 C35 . 1.369(4) ?
C35 C36 . 1.434(3) ?
C35 C37 . 1.501(4) ?
C37 N2 . 1.489(4) ?
C37 C38 . 1.539(3) ?
C37 H37 . 0.9800 ?
C38 C39 . 1.509(4) ?
C38 C51 . 1.518(4) ?
C38 C44 . 1.561(4) ?
C39 O4 . 1.430(3) ?
C39 H39A . 0.9700 ?
C39 H39B . 0.9700 ?
C40 C41A . 1.338(14) ?
C40 N2 . 1.457(4) ?
C40 C41 . 1.493(8) ?
C40 H40A . 0.9700 ?
C40 H40B . 0.9700 ?
C42 C41 . 1.471(7) ?
C42 C43 . 1.492(5) ?
C42 C41A . 1.582(17) ?
C42 H42A . 0.9700 ?
C42 H42B . 0.9700 ?
C43 N2 . 1.463(4) ?
C43 C44 . 1.563(4) ?
C43 H43 . 0.9800 ?
C44 C45 . 1.507(4) ?
C44 H44 . 0.9800 ?
C45 C50 . 1.375(4) ?
C45 C46 . 1.388(4) ?
C46 C47 . 1.375(4) ?
C46 H46 . 0.9300 ?
C47 C48 . 1.365(4) ?
C47 H47 . 0.9300 ?
C48 C49 . 1.364(4) ?
C48 Cl2 . 1.734(3) ?
C49 C50 . 1.378(4) ?
C49 H49 . 0.9300 ?
C50 H50 . 0.9300 ?
C51 O5 . 1.185(3) ?
C51 O6 . 1.301(4) ?
C52 O6 . 1.450(4) ?
C52 H52A . 0.9600 ?
C52 H52B . 0.9600 ?
C52 H52C . 0.9600 ?
C41 H41A . 0.9700 ?
C41 H41B . 0.9700 ?
C41A H41C . 0.9700 ?
C41A H41D . 0.9700 ?
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
_geom_hbond_publ_flag
C11 H11 O3 . 0.98 2.39 2.773(3) 102.8 y
C37 H37 O6 . 0.98 2.48 2.818(3) 100.1 y
C14 H14A Cg12 2_545 0.97 3.00 3.951(2) 168.0 y
C16 H16A Cg11 2_545 0.97 2.83 3.706(2) 151.0 y
C21 H21 Cg11 3_565 0.93 2.85 3.649(2) 144.0 y
C26 H26B Cg5 2_655 0.96 2.83 3.5550(10) 133.0 y
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
C10 C1 C2 C3 . . . . 0.2(4) ?
C1 C2 C3 C4 . . . . 2.1(5) ?
C2 C3 C4 C5 . . . . -1.4(4) ?
C3 C4 C5 C10 . . . . -1.7(4) ?
C3 C4 C5 C6 . . . . 177.3(3) ?
C4 C5 C6 C7 . . . . -179.5(2) ?
C10 C5 C6 C7 . . . . -0.5(4) ?
C5 C6 C7 C8 . . . . -2.3(4) ?
C6 C7 C8 O1 . . . . -179.5(2) ?
C6 C7 C8 C9 . . . . 1.7(4) ?
O1 C8 C9 C10 . . . . -177.1(2) ?
C7 C8 C9 C10 . . . . 1.5(3) ?
O1 C8 C9 C11 . . . . 3.2(4) ?
C7 C8 C9 C11 . . . . -178.2(2) ?
C4 C5 C10 C1 . . . . 3.9(3) ?
C6 C5 C10 C1 . . . . -175.1(2) ?
C4 C5 C10 C9 . . . . -177.2(2) ?
C6 C5 C10 C9 . . . . 3.8(3) ?
C2 C1 C10 C5 . . . . -3.2(4) ?
C2 C1 C10 C9 . . . . 177.9(2) ?
C8 C9 C10 C5 . . . . -4.3(3) ?
C11 C9 C10 C5 . . . . 175.5(2) ?
C8 C9 C10 C1 . . . . 174.6(2) ?
C11 C9 C10 C1 . . . . -5.6(3) ?
C8 C9 C11 N1 . . . . 102.2(2) ?
C10 C9 C11 N1 . . . . -77.5(3) ?
C8 C9 C11 C12 . . . . -14.9(3) ?
C10 C9 C11 C12 . . . . 165.4(2) ?
N1 C11 C12 C25 . . . . 157.0(2) ?
C9 C11 C12 C25 . . . . -80.6(3) ?
N1 C11 C12 C13 . . . . -80.9(2) ?
C9 C11 C12 C13 . . . . 41.5(3) ?
N1 C11 C12 C18 . . . . 36.0(2) ?
C9 C11 C12 C18 . . . . 158.50(19) ?
C25 C12 C13 O1 . . . . 66.2(2) ?
C11 C12 C13 O1 . . . . -60.2(3) ?
C18 C12 C13 O1 . . . . -172.10(19) ?
N1 C14 C15 C16 . . . . -36.6(3) ?
C14 C15 C16 C17 . . . . 35.5(3) ?
C15 C16 C17 N1 . . . . -21.8(3) ?
C15 C16 C17 C18 . . . . -140.6(2) ?
N1 C17 C18 C19 . . . . 153.3(2) ?
C16 C17 C18 C19 . . . . -87.4(3) ?
N1 C17 C18 C12 . . . . 25.6(2) ?
C16 C17 C18 C12 . . . . 144.9(2) ?
C25 C12 C18 C19 . . . . 71.1(3) ?
C13 C12 C18 C19 . . . . -48.9(3) ?
C11 C12 C18 C19 . . . . -164.9(2) ?
C25 C12 C18 C17 . . . . -161.7(2) ?
C13 C12 C18 C17 . . . . 78.3(2) ?
C11 C12 C18 C17 . . . . -37.7(2) ?
C17 C18 C19 C24 . . . . 144.5(3) ?
C12 C18 C19 C24 . . . . -95.1(3) ?
C17 C18 C19 C20 . . . . -36.2(4) ?
C12 C18 C19 C20 . . . . 84.2(3) ?
C24 C19 C20 C21 . . . . 0.2(5) ?
C18 C19 C20 C21 . . . . -179.2(3) ?
C19 C20 C21 C22 . . . . -1.0(5) ?
C20 C21 C22 C23 . . . . 1.6(5) ?
C20 C21 C22 Cl1 . . . . -178.1(2) ?
C21 C22 C23 C24 . . . . -1.3(6) ?
Cl1 C22 C23 C24 . . . . 178.4(3) ?
C20 C19 C24 C23 . . . . 0.1(5) ?
C18 C19 C24 C23 . . . . 179.5(3) ?
C22 C23 C24 C19 . . . . 0.4(5) ?
C13 C12 C25 O2 . . . . 33.3(4) ?
C11 C12 C25 O2 . . . . 155.8(3) ?
C18 C12 C25 O2 . . . . -88.0(3) ?
C13 C12 C25 O3 . . . . -147.2(2) ?
C11 C12 C25 O3 . . . . -24.8(3) ?
C18 C12 C25 O3 . . . . 91.5(3) ?
C36 C27 C28 C29 . . . . 0.4(4) ?
C27 C28 C29 C30 . . . . 0.0(5) ?
C28 C29 C30 C31 . . . . 0.9(5) ?
C29 C30 C31 C32 . . . . 176.5(3) ?
C29 C30 C31 C36 . . . . -2.3(4) ?
C30 C31 C32 C33 . . . . -177.6(3) ?
C36 C31 C32 C33 . . . . 1.2(4) ?
C31 C32 C33 C34 . . . . -1.6(4) ?
C32 C33 C34 O4 . . . . 178.6(3) ?
C32 C33 C34 C35 . . . . -1.3(4) ?
O4 C34 C35 C36 . . . . -175.5(2) ?
C33 C34 C35 C36 . . . . 4.3(4) ?
O4 C34 C35 C37 . . . . 4.3(4) ?
C33 C34 C35 C37 . . . . -175.9(2) ?
C28 C27 C36 C31 . . . . -1.7(4) ?
C28 C27 C36 C35 . . . . -179.8(2) ?
C32 C31 C36 C27 . . . . -176.2(2) ?
C30 C31 C36 C27 . . . . 2.6(4) ?
C32 C31 C36 C35 . . . . 2.0(4) ?
C30 C31 C36 C35 . . . . -179.2(2) ?
C34 C35 C36 C27 . . . . 173.4(2) ?
C37 C35 C36 C27 . . . . -6.4(4) ?
C34 C35 C36 C31 . . . . -4.6(3) ?
C37 C35 C36 C31 . . . . 175.6(2) ?
C34 C35 C37 N2 . . . . 91.9(3) ?
C36 C35 C37 N2 . . . . -88.3(3) ?
C34 C35 C37 C38 . . . . -21.6(3) ?
C36 C35 C37 C38 . . . . 158.2(2) ?
N2 C37 C38 C39 . . . . -73.7(3) ?
C35 C37 C38 C39 . . . . 46.2(3) ?
N2 C37 C38 C51 . . . . 164.0(2) ?
C35 C37 C38 C51 . . . . -76.2(3) ?
N2 C37 C38 C44 . . . . 43.2(3) ?
C35 C37 C38 C44 . . . . 163.0(2) ?
C51 C38 C39 O4 . . . . 68.7(3) ?
C37 C38 C39 O4 . . . . -57.0(3) ?
C44 C38 C39 O4 . . . . -167.5(2) ?
C41 C42 C43 N2 . . . . -28.8(7) ?
C41A C42 C43 N2 . . . . 5.7(11) ?
C41 C42 C43 C44 . . . . -147.6(6) ?
C41A C42 C43 C44 . . . . -113.1(11) ?
C39 C38 C44 C45 . . . . -49.2(3) ?
C51 C38 C44 C45 . . . . 73.0(3) ?
C37 C38 C44 C45 . . . . -164.3(2) ?
C39 C38 C44 C43 . . . . 76.8(3) ?
C51 C38 C44 C43 . . . . -161.0(2) ?
C37 C38 C44 C43 . . . . -38.3(3) ?
N2 C43 C44 C45 . . . . 146.1(3) ?
C42 C43 C44 C45 . . . . -93.8(4) ?
N2 C43 C44 C38 . . . . 19.1(3) ?
C42 C43 C44 C38 . . . . 139.2(3) ?
C38 C44 C45 C50 . . . . -101.4(3) ?
C43 C44 C45 C50 . . . . 139.0(3) ?
C38 C44 C45 C46 . . . . 77.1(4) ?
C43 C44 C45 C46 . . . . -42.5(4) ?
C50 C45 C46 C47 . . . . 1.3(5) ?
C44 C45 C46 C47 . . . . -177.2(3) ?
C45 C46 C47 C48 . . . . -0.9(5) ?
C46 C47 C48 C49 . . . . -1.2(5) ?
C46 C47 C48 Cl2 . . . . 179.5(3) ?
C47 C48 C49 C50 . . . . 2.6(5) ?
Cl2 C48 C49 C50 . . . . -178.0(3) ?
C46 C45 C50 C49 . . . . 0.2(4) ?
C44 C45 C50 C49 . . . . 178.7(3) ?
C48 C49 C50 C45 . . . . -2.1(5) ?
C39 C38 C51 O5 . . . . 20.7(4) ?
C37 C38 C51 O5 . . . . 142.7(3) ?
C44 C38 C51 O5 . . . . -102.6(4) ?
C39 C38 C51 O6 . . . . -163.0(2) ?
C37 C38 C51 O6 . . . . -41.0(4) ?
C44 C38 C51 O6 . . . . 73.7(3) ?
C15 C14 N1 C11 . . . . 147.4(2) ?
C15 C14 N1 C17 . . . . 23.1(3) ?
C9 C11 N1 C14 . . . . 94.5(3) ?
C12 C11 N1 C14 . . . . -143.8(2) ?
C9 C11 N1 C17 . . . . -142.5(2) ?
C12 C11 N1 C17 . . . . -20.8(2) ?
C16 C17 N1 C14 . . . . -0.8(3) ?
C18 C17 N1 C14 . . . . 125.3(2) ?
C16 C17 N1 C11 . . . . -129.4(2) ?
C18 C17 N1 C11 . . . . -3.3(3) ?
C41A C40 N2 C43 . . . . -26.4(14) ?
C41 C40 N2 C43 . . . . 11.5(6) ?
C41A C40 N2 C37 . . . . 97.7(14) ?
C41 C40 N2 C37 . . . . 135.6(6) ?
C42 C43 N2 C40 . . . . 10.8(4) ?
C44 C43 N2 C40 . . . . 137.3(3) ?
C42 C43 N2 C37 . . . . -118.0(3) ?
C44 C43 N2 C37 . . . . 8.4(3) ?
C35 C37 N2 C40 . . . . 84.8(3) ?
C38 C37 N2 C40 . . . . -155.3(3) ?
C35 C37 N2 C43 . . . . -152.7(2) ?
C38 C37 N2 C43 . . . . -32.8(3) ?
C9 C8 O1 C13 . . . . -21.0(3) ?
C7 C8 O1 C13 . . . . 160.3(2) ?
C12 C13 O1 C8 . . . . 50.0(3) ?
O2 C25 O3 C26 . . . . 3.1(5) ?
C12 C25 O3 C26 . . . . -176.4(3) ?
C35 C34 O4 C39 . . . . -14.4(4) ?
C33 C34 O4 C39 . . . . 165.8(2) ?
C38 C39 O4 C34 . . . . 41.8(3) ?
O5 C51 O6 C52 . . . . -1.4(5) ?
C38 C51 O6 C52 . . . . -177.7(3) ?
C43 C42 C41 C40 . . . . 35.3(8) ?
C41A C42 C41 C40 . . . . -57.7(9) ?
C41A C40 C41 C42 . . . . 69.9(11) ?
N2 C40 C41 C42 . . . . -29.8(9) ?
N2 C40 C41A C42 . . . . 30.0(19) ?
C41 C40 C41A C42 . . . . -61.9(14) ?
C41 C42 C41A C40 . . . . 72.3(15) ?
C43 C42 C41A C40 . . . . -22.1(18) ?
