#------------------------------------------------------------------------------
#$Date: 2020-04-09 02:24:16 +0300 (Thu, 09 Apr 2020) $
#$Revision: 250512 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038241.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038241
loop_
_publ_author_name
'Tu, Man-Su'
'Liu, Si-Jia'
'Zhong, Chen'
'Zhang, Shu'
'Zhang, Huiwen'
'Zheng, Yuan-Lin'
'Shi, Feng'
_publ_section_title
;
 Diastereo- and Enantioselective Construction of Biologically Important
 Chiral 1,3-Dioxolochroman Frameworks via Catalytic Asymmetric [4+2]
 Cycloadditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00119
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C33 H26 Cl N O3'
_chemical_formula_sum            'C33 H26 Cl N O3'
_chemical_formula_weight         520.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7682(2)
_cell_length_b                   8.63480(10)
_cell_length_c                   22.2785(3)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      54.63
_cell_measurement_theta_min      4.228
_cell_volume                     2633.39(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      199.97
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38114
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.894
_diffrn_reflns_theta_min         4.227
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1128 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.7870. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.624
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 3586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         9956
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1089P)²+1.0128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                8796
_reflns_number_total             9956
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00119_si_002.cif
_cod_data_source_block           190701sf_0m
_cod_database_code               4038241
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.905
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C1A(H1AB), C2A(H2A), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31),
  C32(H32), C33(H33), N1A(H1AA), C5A(H5A), C8A(H8A), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C21A(H21A), C22A(H22A), C23A(H23A), C24A(H24A),
 C25A(H25A), C26A(H26A), C27A(H27A), C30A(H30A), C31A(H31A), C32A(H32A),
 C33A(H33A)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.22218(17) 0.2316(3) 0.45864(8) 0.1023(7) Uani 1 1 d . . . . .
O1 O 0.2578(2) 0.2660(3) 0.80943(13) 0.0438(7) Uani 1 1 d . . . . .
O2 O 0.6293(3) 0.0622(5) 0.7898(2) 0.0756(12) Uani 1 1 d . . . . .
O3 O 0.5880(3) 0.1347(5) 0.8838(2) 0.0770(12) Uani 1 1 d . . . . .
N1 N 0.0867(3) 0.4529(4) 0.79248(17) 0.0423(8) Uani 1 1 d . . . . .
H1 H 0.133213 0.517315 0.784671 0.051 Uiso 1 1 calc R . . . .
C1 C 0.1772(3) 0.2206(5) 0.76496(17) 0.0395(9) Uani 1 1 d . . . . .
H1A H 0.169349 0.105590 0.766456 0.047 Uiso 1 1 calc R . . . .
C2 C 0.2010(3) 0.2660(5) 0.70208(19) 0.0427(10) Uani 1 1 d . . . . .
H2 H 0.210650 0.380785 0.701786 0.051 Uiso 1 1 calc R . . . .
C3 C 0.2970(4) 0.1900(6) 0.6876(2) 0.0482(11) Uani 1 1 d . . . . .
H3 H 0.282164 0.084373 0.670629 0.058 Uiso 1 1 calc R . . . .
C4 C 0.3719(3) 0.1759(5) 0.7421(2) 0.0452(10) Uani 1 1 d . . . . .
C5 C 0.4666(4) 0.1218(5) 0.7351(3) 0.0539(12) Uani 1 1 d . . . . .
H5 H 0.484649 0.094146 0.696552 0.065 Uiso 1 1 calc R . . . .
C6 C 0.5316(4) 0.1106(6) 0.7860(3) 0.0593(14) Uani 1 1 d . . . . .
C7 C 0.5079(4) 0.1524(6) 0.8416(3) 0.0561(13) Uani 1 1 d . . . . .
C8 C 0.4172(4) 0.2029(5) 0.8507(2) 0.0531(11) Uani 1 1 d . . . . .
H8 H 0.400614 0.229858 0.889640 0.064 Uiso 1 1 calc R . . . .
C9 C 0.3491(3) 0.2131(5) 0.7990(2) 0.0437(9) Uani 1 1 d . . . . .
C10 C 0.6566(5) 0.0440(9) 0.8537(4) 0.0809(19) Uani 1 1 d . . . . .
H10A H 0.724070 0.081639 0.864774 0.097 Uiso 1 1 calc R . . . .
H10B H 0.653262 -0.066357 0.865332 0.097 Uiso 1 1 calc R . . . .
C11 C 0.0880(3) 0.2944(5) 0.78444(17) 0.0394(9) Uani 1 1 d . . . . .
C12 C 0.0022(4) 0.2322(6) 0.7985(2) 0.0479(11) Uani 1 1 d . . . . .
C13 C -0.0550(3) 0.3586(6) 0.8176(2) 0.0477(10) Uani 1 1 d . . . . .
C14 C -0.1483(5) 0.3734(9) 0.8367(3) 0.0750(17) Uani 1 1 d . . . . .
H14 H -0.189372 0.285290 0.837624 0.090 Uiso 1 1 calc R . . . .
C15 C -0.1797(5) 0.5136(11) 0.8539(3) 0.084(2) Uani 1 1 d . . . . .
H15 H -0.242416 0.522171 0.867758 0.100 Uiso 1 1 calc R . . . .
C16 C -0.1215(5) 0.6465(9) 0.8518(3) 0.0720(18) Uani 1 1 d . . . . .
H16 H -0.145454 0.743369 0.864035 0.086 Uiso 1 1 calc R . . . .
C17 C -0.0310(4) 0.6385(7) 0.8322(2) 0.0596(13) Uani 1 1 d . . . . .
H17 H 0.008736 0.728095 0.830692 0.072 Uiso 1 1 calc R . . . .
C18 C 0.0009(3) 0.4936(6) 0.81466(19) 0.0444(10) Uani 1 1 d . . . . .
C19 C -0.0308(5) 0.0687(6) 0.7932(3) 0.0698(16) Uani 1 1 d . . . . .
H19A H -0.065345 0.051341 0.752935 0.105 Uiso 1 1 calc GR . . . .
H19B H -0.074856 0.046986 0.823881 0.105 Uiso 1 1 calc GR . . . .
H19C H 0.025987 -0.000130 0.799133 0.105 Uiso 1 1 calc GR . . . .
C20 C 0.1181(3) 0.2273(6) 0.65342(19) 0.0453(10) Uani 1 1 d . . . . .
C21 C 0.0763(4) 0.0803(6) 0.6494(2) 0.0558(12) Uani 1 1 d . . . . .
H21 H 0.095934 0.005834 0.679681 0.067 Uiso 1 1 calc R . . . .
C22 C 0.0077(5) 0.0405(7) 0.6029(3) 0.0675(15) Uani 1 1 d . . . . .
H22 H -0.020164 -0.060198 0.601441 0.081 Uiso 1 1 calc R . . . .
C23 C -0.0211(4) 0.1472(8) 0.5579(3) 0.0676(16) Uani 1 1 d . . . . .
H23 H -0.067832 0.119609 0.525162 0.081 Uiso 1 1 calc R . . . .
C24 C 0.0182(4) 0.2916(9) 0.5613(2) 0.0707(16) Uani 1 1 d . . . . .
H24 H -0.001732 0.365320 0.530856 0.085 Uiso 1 1 calc R . . . .
C25 C 0.0872(4) 0.3331(7) 0.6087(2) 0.0562(12) Uani 1 1 d . . . . .
H25 H 0.113426 0.434947 0.610366 0.067 Uiso 1 1 calc R . . . .
C26 C 0.3390(4) 0.2880(6) 0.6401(2) 0.0547(11) Uani 1 1 d . . . . .
H26 H 0.369540 0.383001 0.652560 0.066 Uiso 1 1 calc R . . . .
C27 C 0.3359(4) 0.2506(7) 0.5838(2) 0.0602(13) Uani 1 1 d . . . . .
H27 H 0.310636 0.151542 0.571938 0.072 Uiso 1 1 calc R . . . .
C28 C 0.3693(4) 0.3520(6) 0.5365(2) 0.0524(11) Uani 1 1 d . . . . .
C29 C 0.3226(5) 0.3493(7) 0.4776(3) 0.0683(15) Uani 1 1 d . . . . .
C30 C 0.3567(7) 0.4442(9) 0.4316(3) 0.088(2) Uani 1 1 d . . . . .
H30 H 0.324648 0.443248 0.391685 0.105 Uiso 1 1 calc R . . . .
C31 C 0.4362(7) 0.5361(10) 0.4464(4) 0.092(2) Uani 1 1 d . . . . .
H31 H 0.459836 0.599527 0.416294 0.110 Uiso 1 1 calc R . . . .
C32 C 0.4819(6) 0.5384(10) 0.5032(4) 0.089(2) Uani 1 1 d . . . . .
H32 H 0.536222 0.605007 0.512878 0.107 Uiso 1 1 calc R . . . .
C33 C 0.4506(5) 0.4461(7) 0.5463(3) 0.0674(15) Uani 1 1 d . . . . .
H33 H 0.486269 0.446112 0.585281 0.081 Uiso 1 1 calc R . . . .
Cl1A Cl 0.80750(9) 0.80067(16) 0.70808(6) 0.0595(3) Uani 1 1 d . . . . .
O1A O 0.2407(2) 0.6826(4) 0.77329(13) 0.0413(7) Uani 1 1 d . . . . .
O2A O 0.1757(3) 0.7684(5) 0.55970(15) 0.0599(9) Uani 1 1 d . . . . .
O3A O 0.3387(3) 0.8188(5) 0.54832(15) 0.0633(10) Uani 1 1 d . . . . .
N1A N 0.2460(3) 0.5391(4) 0.89704(17) 0.0417(8) Uani 1 1 d . . . . .
H1AA H 0.269961 0.457008 0.880391 0.050 Uiso 1 1 calc R . . . .
C1A C 0.3078(3) 0.7303(5) 0.82528(18) 0.0382(9) Uani 1 1 d . . . . .
H1AB H 0.317656 0.844897 0.823543 0.046 Uiso 1 1 calc R . . . .
C2A C 0.4062(3) 0.6492(5) 0.82186(18) 0.0363(8) Uani 1 1 d . . . . .
H2A H 0.393117 0.535964 0.816238 0.044 Uiso 1 1 calc R . . . .
C3A C 0.4516(3) 0.7085(5) 0.76545(19) 0.0387(9) Uani 1 1 d . . . . .
H3A H 0.482862 0.811251 0.775331 0.046 Uiso 1 1 calc R . . . .
C4A C 0.3724(3) 0.7301(5) 0.71207(18) 0.0386(9) Uani 1 1 d . . . . .
C5A C 0.4002(3) 0.7672(5) 0.6546(2) 0.0451(10) Uani 1 1 d . . . . .
H5A H 0.466799 0.783739 0.648948 0.054 Uiso 1 1 calc R . . . .
C6A C 0.3286(4) 0.7786(5) 0.6072(2) 0.0470(10) Uani 1 1 d . . . . .
C7A C 0.2311(4) 0.7532(5) 0.6143(2) 0.0459(10) Uani 1 1 d . . . . .
C8A C 0.2005(3) 0.7206(5) 0.6689(2) 0.0434(9) Uani 1 1 d . . . . .
H8A H 0.133501 0.704394 0.673785 0.052 Uiso 1 1 calc R . . . .
C9A C 0.2743(3) 0.7123(5) 0.71814(19) 0.0402(9) Uani 1 1 d . . . . .
C10A C 0.2444(5) 0.7943(9) 0.5168(2) 0.0701(15) Uani 1 1 d . . . . .
H10C H 0.245907 0.703412 0.489852 0.084 Uiso 1 1 calc R . . . .
H10D H 0.224631 0.885970 0.491773 0.084 Uiso 1 1 calc R . . . .
C11A C 0.2581(3) 0.6925(5) 0.87951(19) 0.0383(9) Uani 1 1 d . . . . .
C12A C 0.2149(3) 0.7896(5) 0.91707(18) 0.0403(9) Uani 1 1 d . . . . .
C13A C 0.1721(3) 0.6934(5) 0.95981(19) 0.0431(10) Uani 1 1 d . . . . .
C14A C 0.1178(4) 0.7242(8) 1.0085(2) 0.0572(12) Uani 1 1 d . . . . .
H14A H 0.106662 0.827570 1.020697 0.069 Uiso 1 1 calc R . . . .
C15A C 0.0816(4) 0.6012(8) 1.0379(3) 0.0672(15) Uani 1 1 d . . . . .
H15A H 0.044637 0.620574 1.070743 0.081 Uiso 1 1 calc R . . . .
C16A C 0.0971(4) 0.4498(8) 1.0212(3) 0.0674(16) Uani 1 1 d . . . . .
H16A H 0.068797 0.368241 1.042039 0.081 Uiso 1 1 calc R . . . .
C17A C 0.1525(4) 0.4141(6) 0.9750(2) 0.0563(12) Uani 1 1 d . . . . .
H17A H 0.164293 0.309767 0.964381 0.068 Uiso 1 1 calc R . . . .
C18A C 0.1905(3) 0.5380(6) 0.9446(2) 0.0435(10) Uani 1 1 d . . . . .
C19A C 0.2070(4) 0.9628(6) 0.9142(2) 0.0543(12) Uani 1 1 d . . . . .
H19D H 0.255392 1.008740 0.944478 0.082 Uiso 1 1 calc GR . . . .
H19E H 0.141298 0.994313 0.922309 0.082 Uiso 1 1 calc GR . . . .
H19F H 0.219166 0.998414 0.873903 0.082 Uiso 1 1 calc GR . . . .
C20A C 0.4775(3) 0.6689(5) 0.87843(19) 0.0380(9) Uani 1 1 d . . . . .
C21A C 0.5426(3) 0.5531(6) 0.8958(2) 0.0466(10) Uani 1 1 d . . . . .
H21A H 0.540712 0.459531 0.873337 0.056 Uiso 1 1 calc R . . . .
C22A C 0.6111(4) 0.5702(7) 0.9458(2) 0.0561(12) Uani 1 1 d . . . . .
H22A H 0.655893 0.488928 0.956905 0.067 Uiso 1 1 calc R . . . .
C23A C 0.6144(4) 0.7041(7) 0.9791(2) 0.0552(12) Uani 1 1 d . . . . .
H23A H 0.661967 0.716198 1.012930 0.066 Uiso 1 1 calc R . . . .
C24A C 0.5479(4) 0.8215(7) 0.9632(2) 0.0586(13) Uani 1 1 d . . . . .
H24A H 0.549061 0.913752 0.986539 0.070 Uiso 1 1 calc R . . . .
C25A C 0.4796(4) 0.8039(6) 0.9131(2) 0.0498(10) Uani 1 1 d . . . . .
H25A H 0.434001 0.884395 0.902256 0.060 Uiso 1 1 calc R . . . .
C26A C 0.5281(3) 0.6003(5) 0.74675(19) 0.0402(9) Uani 1 1 d . . . . .
H26A H 0.512513 0.493236 0.743386 0.048 Uiso 1 1 calc R . . . .
C27A C 0.6170(3) 0.6449(5) 0.7345(2) 0.0443(10) Uani 1 1 d . . . . .
H27A H 0.633229 0.750854 0.741190 0.053 Uiso 1 1 calc R . . . .
C28A C 0.6914(3) 0.5468(6) 0.71191(19) 0.0438(10) Uani 1 1 d . . . . .
C29A C 0.7811(3) 0.6042(6) 0.6984(2) 0.0457(10) Uani 1 1 d . . . . .
C30A C 0.8520(4) 0.5123(7) 0.6775(2) 0.0569(13) Uani 1 1 d . . . . .
H30A H 0.912302 0.556233 0.669100 0.068 Uiso 1 1 calc R . . . .
C31A C 0.8349(4) 0.3557(8) 0.6687(3) 0.0677(16) Uani 1 1 d . . . . .
H31A H 0.883017 0.291359 0.654005 0.081 Uiso 1 1 calc R . . . .
C32A C 0.7472(5) 0.2943(7) 0.6817(3) 0.0692(15) Uani 1 1 d . . . . .
H32A H 0.735421 0.186456 0.676659 0.083 Uiso 1 1 calc R . . . .
C33A C 0.6769(4) 0.3874(6) 0.7017(3) 0.0608(13) Uani 1 1 d . . . . .
H33A H 0.616188 0.342692 0.708873 0.073 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
Cl Cl 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 115.9(3) . . ?
C6 O2 C10 103.8(5) . . ?
C7 O3 C10 105.0(5) . . ?
C11 N1 H1 125.5 . . ?
C18 N1 H1 125.5 . . ?
C18 N1 C11 108.9(4) . . ?
O1 C1 H1A 108.7 . . ?
O1 C1 C2 109.4(3) . . ?
O1 C1 C11 106.1(3) . . ?
C2 C1 H1A 108.7 . . ?
C11 C1 H1A 108.7 . . ?
C11 C1 C2 115.1(3) . . ?
C1 C2 H2 107.6 . . ?
C1 C2 C3 110.9(3) . . ?
C1 C2 C20 112.2(4) . . ?
C3 C2 H2 107.6 . . ?
C20 C2 H2 107.6 . . ?
C20 C2 C3 110.6(4) . . ?
C2 C3 H3 108.9 . . ?
C4 C3 C2 113.1(4) . . ?
C4 C3 H3 108.9 . . ?
C4 C3 C26 109.1(4) . . ?
C26 C3 C2 108.0(4) . . ?
C26 C3 H3 108.9 . . ?
C5 C4 C3 119.8(4) . . ?
C9 C4 C3 121.2(4) . . ?
C9 C4 C5 119.0(5) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.5(5) . . ?
C6 C5 H5 121.2 . . ?
C5 C6 O2 127.5(6) . . ?
C7 C6 O2 110.2(5) . . ?
C7 C6 C5 122.3(5) . . ?
C6 C7 O3 109.8(5) . . ?
C8 C7 O3 127.9(6) . . ?
C8 C7 C6 122.3(5) . . ?
C7 C8 H8 121.9 . . ?
C7 C8 C9 116.1(5) . . ?
C9 C8 H8 121.9 . . ?
O1 C9 C8 114.9(4) . . ?
C4 C9 O1 122.3(4) . . ?
C4 C9 C8 122.8(5) . . ?
O2 C10 O3 106.5(5) . . ?
O2 C10 H10A 110.4 . . ?
O2 C10 H10B 110.4 . . ?
O3 C10 H10A 110.4 . . ?
O3 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
N1 C11 C1 119.0(4) . . ?
C12 C11 N1 109.6(4) . . ?
C12 C11 C1 131.3(4) . . ?
C11 C12 C13 106.6(4) . . ?
C11 C12 C19 128.4(5) . . ?
C13 C12 C19 125.0(5) . . ?
C14 C13 C12 135.1(5) . . ?
C14 C13 C18 117.6(5) . . ?
C18 C13 C12 107.2(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(7) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.3(6) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(6) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 121.3 . . ?
C16 C17 C18 117.4(6) . . ?
C18 C17 H17 121.3 . . ?
N1 C18 C13 107.5(4) . . ?
N1 C18 C17 129.7(5) . . ?
C17 C18 C13 122.8(5) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C2 121.2(4) . . ?
C25 C20 C2 121.0(5) . . ?
C25 C20 C21 117.5(5) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.6(5) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(6) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.1(5) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 121.1(6) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 C24 120.6(6) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C3 C26 H26 117.9 . . ?
C27 C26 C3 124.3(5) . . ?
C27 C26 H26 117.9 . . ?
C26 C27 H27 117.9 . . ?
C26 C27 C28 124.3(5) . . ?
C28 C27 H27 117.9 . . ?
C29 C28 C27 120.8(5) . . ?
C33 C28 C27 122.9(5) . . ?
C33 C28 C29 116.2(5) . . ?
C28 C29 Cl1 120.9(4) . . ?
C28 C29 C30 120.7(6) . . ?
C30 C29 Cl1 118.5(5) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 C29 118.5(7) . . ?
C31 C30 H30 120.7 . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.0(7) . . ?
C32 C31 H31 119.5 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.3(8) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 H33 118.4 . . ?
C32 C33 C28 123.2(7) . . ?
C32 C33 H33 118.4 . . ?
C9A O1A C1A 114.2(3) . . ?
C7A O2A C10A 105.2(4) . . ?
C6A O3A C10A 104.6(4) . . ?
C11A N1A H1AA 125.8 . . ?
C18A N1A H1AA 125.8 . . ?
C18A N1A C11A 108.4(4) . . ?
O1A C1A H1AB 109.0 . . ?
O1A C1A C2A 108.6(3) . . ?
O1A C1A C11A 106.0(3) . . ?
C2A C1A H1AB 109.0 . . ?
C11A C1A H1AB 109.0 . . ?
C11A C1A C2A 115.2(3) . . ?
C1A C2A H2A 107.7 . . ?
C1A C2A C3A 109.0(3) . . ?
C3A C2A H2A 107.7 . . ?
C20A C2A C1A 113.7(3) . . ?
C20A C2A H2A 107.7 . . ?
C20A C2A C3A 110.7(3) . . ?
C2A C3A H3A 108.4 . . ?
C4A C3A C2A 110.6(3) . . ?
C4A C3A H3A 108.4 . . ?
C26A C3A C2A 112.1(3) . . ?
C26A C3A H3A 108.4 . . ?
C26A C3A C4A 108.8(3) . . ?
C5A C4A C3A 119.4(4) . . ?
C9A C4A C3A 122.1(4) . . ?
C9A C4A C5A 118.5(4) . . ?
C4A C5A H5A 120.9 . . ?
C6A C5A C4A 118.2(4) . . ?
C6A C5A H5A 120.9 . . ?
O3A C6A C7A 110.2(4) . . ?
C5A C6A O3A 128.0(5) . . ?
C5A C6A C7A 121.8(4) . . ?
O2A C7A C6A 109.8(4) . . ?
C8A C7A O2A 128.1(4) . . ?
C8A C7A C6A 122.1(4) . . ?
C7A C8A H8A 122.0 . . ?
C7A C8A C9A 116.0(4) . . ?
C9A C8A H8A 122.0 . . ?
O1A C9A C8A 114.6(4) . . ?
C4A C9A O1A 122.1(4) . . ?
C4A C9A C8A 123.2(4) . . ?
O2A C10A H10C 109.9 . . ?
O2A C10A H10D 109.9 . . ?
O3A C10A O2A 109.1(4) . . ?
O3A C10A H10C 109.9 . . ?
O3A C10A H10D 109.9 . . ?
H10C C10A H10D 108.3 . . ?
N1A C11A C1A 121.0(4) . . ?
C12A C11A N1A 109.8(4) . . ?
C12A C11A C1A 129.1(4) . . ?
C11A C12A C13A 106.7(4) . . ?
C11A C12A C19A 128.4(4) . . ?
C13A C12A C19A 124.8(4) . . ?
C14A C13A C12A 133.7(5) . . ?
C14A C13A C18A 119.2(5) . . ?
C18A C13A C12A 107.1(4) . . ?
C13A C14A H14A 120.9 . . ?
C15A C14A C13A 118.2(6) . . ?
C15A C14A H14A 120.9 . . ?
C14A C15A H15A 119.0 . . ?
C14A C15A C16A 122.0(5) . . ?
C16A C15A H15A 119.0 . . ?
C15A C16A H16A 119.1 . . ?
C17A C16A C15A 121.7(5) . . ?
C17A C16A H16A 119.1 . . ?
C16A C17A H17A 121.5 . . ?
C16A C17A C18A 117.1(5) . . ?
C18A C17A H17A 121.5 . . ?
N1A C18A C13A 107.9(4) . . ?
N1A C18A C17A 130.4(5) . . ?
C17A C18A C13A 121.7(4) . . ?
C12A C19A H19D 109.5 . . ?
C12A C19A H19E 109.5 . . ?
C12A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C21A C20A C2A 119.8(4) . . ?
C21A C20A C25A 118.6(4) . . ?
C25A C20A C2A 121.6(4) . . ?
C20A C21A H21A 119.4 . . ?
C20A C21A C22A 121.1(5) . . ?
C22A C21A H21A 119.4 . . ?
C21A C22A H22A 119.9 . . ?
C23A C22A C21A 120.3(5) . . ?
C23A C22A H22A 119.9 . . ?
C22A C23A H23A 120.2 . . ?
C22A C23A C24A 119.7(4) . . ?
C24A C23A H23A 120.2 . . ?
C23A C24A H24A 120.1 . . ?
C23A C24A C25A 119.8(5) . . ?
C25A C24A H24A 120.1 . . ?
C20A C25A H25A 119.7 . . ?
C24A C25A C20A 120.5(5) . . ?
C24A C25A H25A 119.7 . . ?
C3A C26A H26A 117.9 . . ?
C27A C26A C3A 124.2(4) . . ?
C27A C26A H26A 117.9 . . ?
C26A C27A H27A 116.8 . . ?
C26A C27A C28A 126.4(4) . . ?
C28A C27A H27A 116.8 . . ?
C29A C28A C27A 122.6(4) . . ?
C29A C28A C33A 115.3(5) . . ?
C33A C28A C27A 122.1(4) . . ?
C28A C29A Cl1A 119.9(4) . . ?
C30A C29A Cl1A 117.1(4) . . ?
C30A C29A C28A 123.0(5) . . ?
C29A C30A H30A 120.2 . . ?
C29A C30A C31A 119.7(5) . . ?
C31A C30A H30A 120.2 . . ?
C30A C31A H31A 120.4 . . ?
C32A C31A C30A 119.1(5) . . ?
C32A C31A H31A 120.4 . . ?
C31A C32A H32A 119.7 . . ?
C33A C32A C31A 120.5(6) . . ?
C33A C32A H32A 119.7 . . ?
C28A C33A H33A 118.8 . . ?
C32A C33A C28A 122.3(5) . . ?
C32A C33A H33A 118.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C29 1.732(7) . ?
O1 C1 1.460(5) . ?
O1 C9 1.381(6) . ?
O2 C6 1.402(6) . ?
O2 C10 1.441(9) . ?
O3 C7 1.379(6) . ?
O3 C10 1.446(9) . ?
N1 H1 0.8800 . ?
N1 C11 1.380(6) . ?
N1 C18 1.374(6) . ?
C1 H1A 1.0000 . ?
C1 C2 1.524(6) . ?
C1 C11 1.488(6) . ?
C2 H2 1.0000 . ?
C2 C3 1.540(6) . ?
C2 C20 1.525(7) . ?
C3 H3 1.0000 . ?
C3 C4 1.513(7) . ?
C3 C26 1.517(7) . ?
C4 C5 1.409(7) . ?
C4 C9 1.375(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(8) . ?
C6 C7 1.362(8) . ?
C7 C8 1.359(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.407(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.365(6) . ?
C12 C13 1.437(7) . ?
C12 C19 1.484(7) . ?
C13 C14 1.401(8) . ?
C13 C18 1.402(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.355(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.403(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.365(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.396(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.392(7) . ?
C20 C25 1.385(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.369(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.358(10) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.292(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.480(7) . ?
C28 C29 1.398(8) . ?
C28 C33 1.382(8) . ?
C29 C30 1.429(9) . ?
C30 H30 0.9500 . ?
C30 C31 1.364(12) . ?
C31 H31 0.9500 . ?
C31 C32 1.352(12) . ?
C32 H32 0.9500 . ?
C32 C33 1.354(9) . ?
C33 H33 0.9500 . ?
Cl1A C29A 1.743(5) . ?
O1A C1A 1.461(5) . ?
O1A C9A 1.382(5) . ?
O2A C7A 1.371(5) . ?
O2A C10A 1.432(7) . ?
O3A C6A 1.379(5) . ?
O3A C10A 1.424(7) . ?
N1A H1AA 0.8800 . ?
N1A C11A 1.396(6) . ?
N1A C18A 1.373(6) . ?
C1A H1AB 1.0000 . ?
C1A C2A 1.534(6) . ?
C1A C11A 1.487(6) . ?
C2A H2A 1.0000 . ?
C2A C3A 1.550(5) . ?
C2A C20A 1.522(6) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.537(6) . ?
C3A C26A 1.500(6) . ?
C4A C5A 1.412(6) . ?
C4A C9A 1.379(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.367(6) . ?
C6A C7A 1.386(7) . ?
C7A C8A 1.360(7) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.415(6) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C12A 1.365(6) . ?
C12A C13A 1.437(6) . ?
C12A C19A 1.500(6) . ?
C13A C14A 1.407(6) . ?
C13A C18A 1.413(7) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.369(8) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.382(10) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.379(9) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.397(7) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A C21A 1.371(6) . ?
C20A C25A 1.397(7) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.387(7) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.372(8) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.386(8) . ?
C24A H24A 0.9500 . ?
C24A C25A 1.390(7) . ?
C25A H25A 0.9500 . ?
C26A H26A 0.9500 . ?
C26A C27A 1.338(6) . ?
C27A H27A 0.9500 . ?
C27A C28A 1.460(6) . ?
C28A C29A 1.393(6) . ?
C28A C33A 1.406(7) . ?
C29A C30A 1.378(7) . ?
C30A H30A 0.9500 . ?
C30A C31A 1.382(9) . ?
C31A H31A 0.9500 . ?
C31A C32A 1.377(9) . ?
C32A H32A 0.9500 . ?
C32A C33A 1.369(8) . ?
C33A H33A 0.9500 . ?
