#------------------------------------------------------------------------------
#$Date: 2019-11-03 11:36:20 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/81/4128155.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_4128155
loop_
_publ_author_name
'Feng, Zhengao'
'Allred, Tyler K.'
'Hurlow, Evan E.'
'Harran, Patrick G.'
_publ_section_title
;
 Anomalous Chromophore Disruption Enables an Eight-Step Synthesis and
 Stereochemical Reassignment of (+)-Marineosin A.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2274
_journal_page_last               2278
_journal_paper_doi               10.1021/jacs.9b00396
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C26.50 H37.50 Cl N3 O2'
_chemical_formula_sum            'C26.5 H37.5 Cl N3 O2'
_chemical_formula_weight         465.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 129.718(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.1593(15)
_cell_length_b                   8.7821(4)
_cell_length_c                   23.3882(10)
_cell_measurement_reflns_used    9065
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.27
_cell_measurement_theta_min      2.68
_cell_volume                     5238.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38002
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.424
_diffrn_reflns_theta_min         2.456
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    1.493
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       needle
_exptl_crystal_F_000             2004
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 3207 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.015(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         9489
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                7892
_reflns_number_total             9489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b00396_si_004.cif
_cod_data_source_block           cu_har1802lts
_cod_original_formula_sum        'C26.50 H37.50 Cl N3 O2'
_cod_database_code               4128155
_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. 
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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 0.64067(4) 0.54421(12) 0.64040(6) 0.0362(2) Uani 1 1 d . . . . .
O1 O 0.82486(11) 0.6635(3) 0.81576(16) 0.0311(6) Uani 1 1 d . . . . .
O2 O 0.89078(11) 0.4014(3) 0.85784(15) 0.0300(6) Uani 1 1 d . . . . .
N1 N 0.72214(12) 0.3144(3) 0.63308(17) 0.0255(7) Uani 1 1 d . . . . .
H1 H 0.7001 0.3638 0.6338 0.031 Uiso 1 1 calc R U . . .
N2 N 0.75881(12) 0.4798(3) 0.77441(17) 0.0227(7) Uani 1 1 d . . . . .
H2 H 0.7292 0.5260 0.7455 0.027 Uiso 1 1 calc R U . . .
N3 N 0.67978(13) 0.3394(4) 0.77727(18) 0.0272(7) Uani 1 1 d . . . . .
H3 H 0.6654 0.4099 0.7441 0.033 Uiso 1 1 calc R U . . .
C1 C 0.77334(15) 0.3570(4) 0.6705(2) 0.0231(8) Uani 1 1 d . . . . .
C2 C 0.79535(17) 0.2473(4) 0.6563(2) 0.0283(9) Uani 1 1 d . . . . .
H2 H 0.8299 0.2453 0.6750 0.034 Uiso 1 1 calc R U . . .
C3 C 0.75631(16) 0.1372(4) 0.6083(2) 0.0286(9) Uani 1 1 d . . . . .
H3 H 0.7606 0.0506 0.5898 0.034 Uiso 1 1 calc R U . . .
C4 C 0.71119(16) 0.1821(4) 0.5944(2) 0.0280(9) Uani 1 1 d . . . . .
C5 C 0.65696(17) 0.1179(6) 0.5427(2) 0.0424(11) Uani 1 1 d . . . . .
H5A H 0.6455 0.0931 0.5707 0.051 Uiso 1 1 calc R U . . .
H5B H 0.6576 0.0242 0.5213 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6171(2) 0.2283(7) 0.4793(3) 0.0590(15) Uani 1 1 d . . . . .
H6A H 0.5833 0.1780 0.4473 0.071 Uiso 1 1 calc R U . . .
H6B H 0.6135 0.3160 0.5010 0.071 Uiso 1 1 calc R U . . .
C7 C 0.6300(2) 0.2848(7) 0.4315(3) 0.0571(14) Uani 1 1 d . . . . .
H7A H 0.6425 0.1986 0.4207 0.069 Uiso 1 1 calc R U . . .
H7B H 0.5977 0.3189 0.3846 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6695(2) 0.4108(6) 0.4614(3) 0.0484(12) Uani 1 1 d . . . . .
H8A H 0.6733 0.4335 0.4244 0.058 Uiso 1 1 calc R U . . .
H8B H 0.7031 0.3728 0.5051 0.058 Uiso 1 1 calc R U . . .
C9 C 0.65797(19) 0.5613(6) 0.4825(3) 0.0458(12) Uani 1 1 d . . . . .
H9A H 0.6247 0.6013 0.4390 0.055 Uiso 1 1 calc R U . . .
H9B H 0.6546 0.5404 0.5200 0.055 Uiso 1 1 calc R U . . .
C10 C 0.6998(2) 0.6812(5) 0.5119(2) 0.0410(11) Uani 1 1 d . . . . .
H10A H 0.6882 0.7742 0.5200 0.049 Uiso 1 1 calc R U . . .
H10B H 0.7026 0.7023 0.4738 0.049 Uiso 1 1 calc R U . . .
C11 C 0.75480(18) 0.6414(5) 0.5844(2) 0.0367(10) Uani 1 1 d . . . . .
H11A H 0.7797 0.7146 0.5918 0.044 Uiso 1 1 calc R U . . .
H11B H 0.7646 0.5418 0.5788 0.044 Uiso 1 1 calc R U . . .
C12 C 0.75958(17) 0.6399(4) 0.6546(2) 0.0304(9) Uani 1 1 d . . . . .
H12 H 0.7244 0.6251 0.6386 0.036 Uiso 1 1 calc R U . . .
C13 C 0.78081(19) 0.7903(5) 0.6968(3) 0.0382(11) Uani 1 1 d . . . . .
H13A H 0.8135 0.8136 0.7071 0.046 Uiso 1 1 calc R U . . .
H13B H 0.7561 0.8708 0.6655 0.046 Uiso 1 1 calc R U . . .
C14 C 0.79036(19) 0.7885(4) 0.7697(3) 0.0365(10) Uani 1 1 d . . . . .
H14 H 0.7568 0.7748 0.7589 0.044 Uiso 1 1 calc R U . . .
C15 C 0.80508(15) 0.5196(4) 0.7822(2) 0.0241(8) Uani 1 1 d . . . . .
C16 C 0.79446(16) 0.5078(4) 0.7074(2) 0.0246(8) Uani 1 1 d . . . . .
H16 H 0.8284 0.5194 0.7191 0.030 Uiso 1 1 calc R U . . .
C17 C 0.8164(2) 0.9314(5) 0.8155(3) 0.0491(13) Uani 1 1 d . . . . .
H17A H 0.8479 0.9503 0.8228 0.074 Uiso 1 1 calc R U . . .
H17B H 0.8248 0.9186 0.8628 0.074 Uiso 1 1 calc R U . . .
H17C H 0.7929 1.0161 0.7898 0.074 Uiso 1 1 calc R U . . .
C18 C 0.84338(15) 0.4019(4) 0.8383(2) 0.0240(8) Uani 1 1 d . . . . .
C19 C 0.82226(16) 0.3141(4) 0.8604(2) 0.0247(8) Uani 1 1 d . . . . .
H19 H 0.8389 0.2373 0.8960 0.030 Uiso 1 1 calc R U . . .
C20 C 0.76852(15) 0.3634(4) 0.8176(2) 0.0225(8) Uani 1 1 d . . . . .
C21 C 0.73160(15) 0.2953(4) 0.8208(2) 0.0230(8) Uani 1 1 d . . . . .
C22 C 0.73842(16) 0.1772(4) 0.8664(2) 0.0284(9) Uani 1 1 d . . . . .
H22 H 0.7694 0.1244 0.9014 0.034 Uiso 1 1 calc R U . . .
C23 C 0.69079(17) 0.1532(4) 0.8502(2) 0.0332(10) Uani 1 1 d . . . . .
H23 H 0.6839 0.0817 0.8724 0.040 Uiso 1 1 calc R U . . .
C24 C 0.65522(17) 0.2552(5) 0.7948(2) 0.0327(9) Uani 1 1 d . . . . .
H24 H 0.6201 0.2639 0.7733 0.039 Uiso 1 1 calc R U . . .
C25 C 0.92532(16) 0.2822(5) 0.9094(2) 0.0327(9) Uani 1 1 d . . . . .
H25A H 0.9303 0.2929 0.9544 0.049 Uiso 1 1 calc R U . . .
H25B H 0.9586 0.2901 0.9205 0.049 Uiso 1 1 calc R U . . .
H25C H 0.9100 0.1847 0.8875 0.049 Uiso 1 1 calc R U . . .
Cl2 Cl 0.61743(4) 0.61278(11) 0.96926(5) 0.0332(2) Uani 1 1 d . . . . .
O3 O 0.48184(10) 0.7543(3) 0.71178(15) 0.0258(6) Uani 1 1 d . . . . .
O4 O 0.48401(11) 0.5709(3) 0.61477(15) 0.0331(7) Uani 1 1 d . . . . .
N4 N 0.56976(12) 0.3221(3) 0.84790(17) 0.0237(7) Uani 1 1 d . . . . .
H4 H 0.5823 0.3886 0.8826 0.028 Uiso 1 1 calc R U . . .
N5 N 0.56901(12) 0.6676(3) 0.80487(17) 0.0225(7) Uani 1 1 d . . . . .
H5 H 0.5774 0.6861 0.8474 0.027 Uiso 1 1 calc R U . . .
N6 N 0.68171(13) 0.7297(4) 0.91895(18) 0.0294(8) Uani 1 1 d . . . . .
H6A H 0.6678 0.7226 0.9397 0.035 Uiso 1 1 calc R U . . .
C26 C 0.52899(15) 0.3475(4) 0.7734(2) 0.0224(8) Uani 1 1 d . . . . .
C27 C 0.52157(16) 0.2169(4) 0.7363(2) 0.0263(8) Uani 1 1 d . . . . .
H27 H 0.4968 0.2021 0.6852 0.032 Uiso 1 1 calc R U . . .
C28 C 0.55857(15) 0.1066(4) 0.7898(2) 0.0258(8) Uani 1 1 d . . . . .
H28 H 0.5623 0.0074 0.7798 0.031 Uiso 1 1 calc R U . . .
C29 C 0.58759(15) 0.1737(4) 0.8586(2) 0.0240(8) Uani 1 1 d . . . . .
C30 C 0.62935(16) 0.1126(5) 0.9348(2) 0.0312(9) Uani 1 1 d . . . . .
H30A H 0.6627 0.1565 0.9536 0.037 Uiso 1 1 calc R U . . .
H30B H 0.6317 0.0034 0.9312 0.037 Uiso 1 1 calc R U . . .
C31 C 0.62118(18) 0.1433(5) 0.9913(2) 0.0362(10) Uani 1 1 d . U . . .
H31A H 0.6525 0.1118 1.0400 0.043 Uiso 1 1 calc R U . . .
H31B H 0.6173 0.2522 0.9933 0.043 Uiso 1 1 calc R U . . .
C32 C 0.57397(19) 0.0636(5) 0.9752(3) 0.0442(11) Uani 1 1 d . U . . .
H32A H 0.5745 -0.0420 0.9635 0.053 Uiso 0.842(8) 1 calc R U P A 1
H32B H 0.5786 0.0644 1.0205 0.053 Uiso 0.842(8) 1 calc R U P A 1
H32C H 0.5561 0.0094 0.9286 0.053 Uiso 0.158(8) 1 calc R U P A 2
H32D H 0.5874 -0.0127 1.0135 0.053 Uiso 0.158(8) 1 calc R U P A 2
C33 C 0.5212(2) 0.1264(6) 0.9145(3) 0.0355(13) Uani 0.842(8) 1 d . U P A 1
H33A H 0.4951 0.0598 0.9080 0.043 Uiso 0.842(8) 1 calc R U P A 1
H33B H 0.5160 0.1234 0.8688 0.043 Uiso 0.842(8) 1 calc R U P A 1
C33A C 0.5337(11) 0.152(3) 0.9701(16) 0.033(5) Uani 0.158(8) 1 d . U P A 2
H33C H 0.5050 0.0830 0.9521 0.039 Uiso 0.158(8) 1 calc R U P A 2
H33D H 0.5489 0.1796 1.0205 0.039 Uiso 0.158(8) 1 calc R U P A 2
C34 C 0.51068(18) 0.2899(5) 0.9258(2) 0.0367(10) Uani 1 1 d . U . . .
H34A H 0.5155 0.2935 0.9713 0.044 Uiso 0.842(8) 1 calc R U P A 1
H34B H 0.5364 0.3572 0.9320 0.044 Uiso 0.842(8) 1 calc R U P A 1
H34C H 0.5385 0.3532 0.9358 0.044 Uiso 0.158(8) 1 calc R U P A 2
H34D H 0.4939 0.3460 0.9412 0.044 Uiso 0.158(8) 1 calc R U P A 2
C35 C 0.4561(2) 0.3493(6) 0.8621(3) 0.0376(14) Uani 0.842(8) 1 d . U P A 1
H35A H 0.4304 0.2764 0.8527 0.045 Uiso 0.842(8) 1 calc R U P A 1
H35B H 0.4506 0.4438 0.8777 0.045 Uiso 0.842(8) 1 calc R U P A 1
C35A C 0.4702(11) 0.262(3) 0.8416(15) 0.035(6) Uani 0.158(8) 1 d . U P A 2
H35C H 0.4872 0.1976 0.8287 0.042 Uiso 0.158(8) 1 calc R U P A 2
H35D H 0.4424 0.2008 0.8333 0.042 Uiso 0.158(8) 1 calc R U P A 2
C36 C 0.44620(17) 0.3773(5) 0.7904(2) 0.0344(10) Uani 1 1 d . U . . .
H36A H 0.4089 0.3924 0.7510 0.041 Uiso 0.842(8) 1 calc R U P A 1
H36B H 0.4562 0.2868 0.7783 0.041 Uiso 0.842(8) 1 calc R U P A 1
H36C H 0.4197 0.4186 0.7917 0.041 Uiso 0.158(8) 1 calc R U P A 2
H36D H 0.4276 0.3299 0.7420 0.041 Uiso 0.158(8) 1 calc R U P A 2
C37 C 0.47566(15) 0.5153(4) 0.7916(2) 0.0259(8) Uani 1 1 d . . . . .
H37 H 0.5066 0.5361 0.8432 0.031 Uiso 1 1 calc R U . . .
C38 C 0.44062(16) 0.6558(4) 0.7599(2) 0.0284(9) Uani 1 1 d . . . . .
H38A H 0.4085 0.6326 0.7104 0.034 Uiso 1 1 calc R U . . .
H38B H 0.4314 0.6806 0.7907 0.034 Uiso 1 1 calc R U . . .
C39 C 0.46637(16) 0.7938(4) 0.7557(2) 0.0276(9) Uani 1 1 d . . . . .
H39 H 0.4973 0.8239 0.8059 0.033 Uiso 1 1 calc R U . . .
C40 C 0.51588(14) 0.6292(4) 0.7376(2) 0.0216(7) Uani 1 1 d . . . . .
C41 C 0.49367(15) 0.4840(4) 0.7463(2) 0.0239(8) Uani 1 1 d . . . . .
H41 H 0.4619 0.4580 0.6961 0.029 Uiso 1 1 calc R U . . .
C42 C 0.42963(17) 0.9274(5) 0.7165(3) 0.0377(10) Uani 1 1 d . . . . .
H42A H 0.4471 1.0086 0.7125 0.057 Uiso 1 1 calc R U . . .
H42B H 0.4192 0.9618 0.7443 0.057 Uiso 1 1 calc R U . . .
H42C H 0.3992 0.8970 0.6677 0.057 Uiso 1 1 calc R U . . .
C43 C 0.52529(15) 0.6087(4) 0.6829(2) 0.0269(8) Uani 1 1 d . . . . .
C44 C 0.57578(15) 0.6364(4) 0.7147(2) 0.0264(8) Uani 1 1 d . . . . .
H44 H 0.5903 0.6342 0.6914 0.032 Uiso 1 1 calc R U . . .
C45 C 0.60267(15) 0.6702(4) 0.7916(2) 0.0231(8) Uani 1 1 d . . . . .
C46 C 0.65653(16) 0.7039(4) 0.8449(2) 0.0257(8) Uani 1 1 d . . . . .
C47 C 0.69238(16) 0.7291(4) 0.8337(3) 0.0314(9) Uani 1 1 d . . . . .
H47 H 0.6860 0.7203 0.7890 0.038 Uiso 1 1 calc R U . . .
C48 C 0.73970(17) 0.7703(5) 0.9022(3) 0.0402(11) Uani 1 1 d . . . . .
H48 H 0.7707 0.7948 0.9115 0.048 Uiso 1 1 calc R U . . .
C49 C 0.73200(17) 0.7681(5) 0.9535(3) 0.0384(11) Uani 1 1 d . . . . .
H49 H 0.7574 0.7896 1.0038 0.046 Uiso 1 1 calc R U . . .
C50 C 0.4925(2) 0.5562(7) 0.5617(3) 0.0501(13) Uani 1 1 d . . . . .
H50A H 0.5073 0.6488 0.5606 0.075 Uiso 1 1 calc R U . . .
H50B H 0.4597 0.5367 0.5133 0.075 Uiso 1 1 calc R U . . .
H50C H 0.5161 0.4733 0.5760 0.075 Uiso 1 1 calc R U . . .
C1S C 0.5290(4) 0.041(2) 0.5288(7) 0.196(7) Uani 1 1 d . U . . .
H1S1 H 0.5422 -0.0451 0.5191 0.236 Uiso 1 1 calc R U . . .
H1S2 H 0.5419 0.1324 0.5222 0.236 Uiso 1 1 calc R U . . .
C2S C 0.6074(6) -0.0222(17) 0.6522(7) 0.195(6) Uani 1 1 d . U . . .
H2S1 H 0.6226 -0.0269 0.7035 0.292 Uiso 1 1 calc R U . . .
H2S2 H 0.6077 -0.1218 0.6355 0.292 Uiso 1 1 calc R U . . .
H2S3 H 0.6273 0.0464 0.6468 0.292 Uiso 1 1 calc R U . . .
C3S C 0.5521(6) 0.0336(19) 0.6064(7) 0.204(7) Uani 1 1 d . U . . .
H3S1 H 0.5318 -0.0348 0.6120 0.245 Uiso 1 1 calc R U . . .
H3S2 H 0.5515 0.1338 0.6234 0.245 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C15 O1 C14 113.6(3) . .
C18 O2 C25 114.9(3) . .
C4 N1 C1 110.4(3) . .
C4 N1 H1 124.8 . .
C1 N1 H1 124.8 . .
C20 N2 C15 111.4(3) . .
C20 N2 H2 124.3 . .
C15 N2 H2 124.3 . .
C24 N3 C21 109.4(3) . .
C24 N3 H3 125.3 . .
C21 N3 H3 125.3 . .
C2 C1 N1 106.6(3) . .
C2 C1 C16 129.7(4) . .
N1 C1 C16 122.9(3) . .
C1 C2 C3 108.2(4) . .
C1 C2 H2 125.9 . .
C3 C2 H2 125.9 . .
C4 C3 C2 107.3(3) . .
C4 C3 H3 126.3 . .
C2 C3 H3 126.3 . .
C3 C4 N1 107.4(4) . .
C3 C4 C5 130.6(4) . .
N1 C4 C5 121.9(4) . .
C4 C5 C6 112.9(4) . .
C4 C5 H5A 109.0 . .
C6 C5 H5A 109.0 . .
C4 C5 H5B 109.0 . .
C6 C5 H5B 109.0 . .
H5A C5 H5B 107.8 . .
C7 C6 C5 116.2(5) . .
C7 C6 H6A 108.2 . .
C5 C6 H6A 108.2 . .
C7 C6 H6B 108.2 . .
C5 C6 H6B 108.2 . .
H6A C6 H6B 107.4 . .
C8 C7 C6 118.1(5) . .
C8 C7 H7A 107.8 . .
C6 C7 H7A 107.8 . .
C8 C7 H7B 107.8 . .
C6 C7 H7B 107.8 . .
H7A C7 H7B 107.1 . .
C7 C8 C9 117.3(5) . .
C7 C8 H8A 108.0 . .
C9 C8 H8A 108.0 . .
C7 C8 H8B 108.0 . .
C9 C8 H8B 108.0 . .
H8A C8 H8B 107.2 . .
C10 C9 C8 113.5(4) . .
C10 C9 H9A 108.9 . .
C8 C9 H9A 108.9 . .
C10 C9 H9B 108.9 . .
C8 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C9 C10 C11 116.1(3) . .
C9 C10 H10A 108.3 . .
C11 C10 H10A 108.3 . .
C9 C10 H10B 108.3 . .
C11 C10 H10B 108.3 . .
H10A C10 H10B 107.4 . .
C10 C11 C12 114.7(4) . .
C10 C11 H11A 108.6 . .
C12 C11 H11A 108.6 . .
C10 C11 H11B 108.6 . .
C12 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
C13 C12 C16 109.5(3) . .
C13 C12 C11 111.8(3) . .
C16 C12 C11 111.8(3) . .
C13 C12 H12 107.9 . .
C16 C12 H12 107.9 . .
C11 C12 H12 107.9 . .
C14 C13 C12 113.3(3) . .
C14 C13 H13A 108.9 . .
C12 C13 H13A 108.9 . .
C14 C13 H13B 108.9 . .
C12 C13 H13B 108.9 . .
H13A C13 H13B 107.7 . .
O1 C14 C17 106.3(4) . .
O1 C14 C13 110.0(3) . .
C17 C14 C13 113.7(4) . .
O1 C14 H14 108.9 . .
C17 C14 H14 108.9 . .
C13 C14 H14 108.9 . .
O1 C15 N2 111.2(3) . .
O1 C15 C18 107.3(3) . .
N2 C15 C18 100.2(3) . .
O1 C15 C16 112.2(3) . .
N2 C15 C16 112.2(3) . .
C18 C15 C16 113.1(3) . .
C1 C16 C12 111.7(3) . .
C1 C16 C15 113.4(3) . .
C12 C16 C15 111.4(3) . .
C1 C16 H16 106.6 . .
C12 C16 H16 106.6 . .
C15 C16 H16 106.6 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O2 C18 C19 131.1(4) . .
O2 C18 C15 117.1(3) . .
C19 C18 C15 111.8(3) . .
C18 C19 C20 106.0(3) . .
C18 C19 H19 127.0 . .
C20 C19 H19 127.0 . .
N2 C20 C21 125.0(4) . .
N2 C20 C19 110.6(3) . .
C21 C20 C19 124.5(3) . .
N3 C21 C22 106.8(3) . .
N3 C21 C20 123.8(3) . .
C22 C21 C20 129.3(4) . .
C23 C22 C21 107.7(4) . .
C23 C22 H22 126.2 . .
C21 C22 H22 126.2 . .
C22 C23 C24 107.3(4) . .
C22 C23 H23 126.3 . .
C24 C23 H23 126.3 . .
N3 C24 C23 108.8(4) . .
N3 C24 H24 125.6 . .
C23 C24 H24 125.6 . .
O2 C25 H25A 109.5 . .
O2 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
O2 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C40 O3 C39 115.6(3) . .
C43 O4 C50 116.1(3) . .
C26 N4 C29 109.9(3) . .
C26 N4 H4 125.0 . .
C29 N4 H4 125.0 . .
C45 N5 C40 111.3(3) . .
C45 N5 H5 124.3 . .
C40 N5 H5 124.3 . .
C49 N6 C46 108.5(3) . .
C49 N6 H6A 125.8 . .
C46 N6 H6A 125.8 . .
C27 C26 N4 107.5(3) . .
C27 C26 C41 128.8(4) . .
N4 C26 C41 122.2(3) . .
C26 C27 C28 107.9(3) . .
C26 C27 H27 126.0 . .
C28 C27 H27 126.0 . .
C29 C28 C27 107.6(3) . .
C29 C28 H28 126.2 . .
C27 C28 H28 126.2 . .
C28 C29 N4 107.1(3) . .
C28 C29 C30 131.7(4) . .
N4 C29 C30 121.2(3) . .
C29 C30 C31 115.2(4) . .
C29 C30 H30A 108.5 . .
C31 C30 H30A 108.5 . .
C29 C30 H30B 108.5 . .
C31 C30 H30B 108.5 . .
H30A C30 H30B 107.5 . .
C32 C31 C30 115.2(4) . .
C32 C31 H31A 108.5 . .
C30 C31 H31A 108.5 . .
C32 C31 H31B 108.5 . .
C30 C31 H31B 108.5 . .
H31A C31 H31B 107.5 . .
C33A C32 C31 120.6(10) . .
C33 C32 C31 117.5(4) . .
C33 C32 H32A 107.9 . .
C31 C32 H32A 107.9 . .
C33 C32 H32B 107.9 . .
C31 C32 H32B 107.9 . .
H32A C32 H32B 107.2 . .
C33A C32 H32C 107.2 . .
C31 C32 H32C 107.2 . .
C33A C32 H32D 107.2 . .
C31 C32 H32D 107.2 . .
H32C C32 H32D 106.8 . .
C32 C33 C34 116.1(4) . .
C32 C33 H33A 108.3 . .
C34 C33 H33A 108.3 . .
C32 C33 H33B 108.3 . .
C34 C33 H33B 108.3 . .
H33A C33 H33B 107.4 . .
C34 C33A C32 121.9(17) . .
C34 C33A H33C 106.9 . .
C32 C33A H33C 106.9 . .
C34 C33A H33D 106.9 . .
C32 C33A H33D 106.9 . .
H33C C33A H33D 106.7 . .
C33A C34 C35A 114.3(16) . .
C35 C34 C33 114.2(4) . .
C35 C34 H34A 108.7 . .
C33 C34 H34A 108.7 . .
C35 C34 H34B 108.7 . .
C33 C34 H34B 108.7 . .
H34A C34 H34B 107.6 . .
C33A C34 H34C 108.7 . .
C35A C34 H34C 108.7 . .
C33A C34 H34D 108.7 . .
C35A C34 H34D 108.7 . .
H34C C34 H34D 107.6 . .
C36 C35 C34 114.8(4) . .
C36 C35 H35A 108.6 . .
C34 C35 H35A 108.6 . .
C36 C35 H35B 108.6 . .
C34 C35 H35B 108.6 . .
H35A C35 H35B 107.5 . .
C36 C35A C34 123(2) . .
C36 C35A H35C 106.6 . .
C34 C35A H35C 106.6 . .
C36 C35A H35D 106.6 . .
C34 C35A H35D 106.6 . .
H35C C35A H35D 106.6 . .
C35A C36 C37 123.9(13) . .
C35 C36 C37 114.9(4) . .
C35 C36 H36A 108.5 . .
C37 C36 H36A 108.5 . .
C35 C36 H36B 108.5 . .
C37 C36 H36B 108.5 . .
H36A C36 H36B 107.5 . .
C35A C36 H36C 106.4 . .
C37 C36 H36C 106.4 . .
C35A C36 H36D 106.4 . .
C37 C36 H36D 106.4 . .
H36C C36 H36D 106.4 . .
C38 C37 C41 108.7(3) . .
C38 C37 C36 110.5(3) . .
C41 C37 C36 111.5(3) . .
C38 C37 H37 108.7 . .
C41 C37 H37 108.7 . .
C36 C37 H37 108.7 . .
C39 C38 C37 113.1(3) . .
C39 C38 H38A 109.0 . .
C37 C38 H38A 109.0 . .
C39 C38 H38B 109.0 . .
C37 C38 H38B 109.0 . .
H38A C38 H38B 107.8 . .
O3 C39 C42 105.6(3) . .
O3 C39 C38 108.8(3) . .
C42 C39 C38 113.0(3) . .
O3 C39 H39 109.8 . .
C42 C39 H39 109.8 . .
C38 C39 H39 109.8 . .
O3 C40 N5 111.4(3) . .
O3 C40 C43 105.8(3) . .
N5 C40 C43 100.3(3) . .
O3 C40 C41 112.5(3) . .
N5 C40 C41 113.3(3) . .
C43 C40 C41 112.7(3) . .
C26 C41 C37 113.1(3) . .
C26 C41 C40 113.9(3) . .
C37 C41 C40 111.7(3) . .
C26 C41 H41 105.8 . .
C37 C41 H41 105.8 . .
C40 C41 H41 105.8 . .
C39 C42 H42A 109.5 . .
C39 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C39 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
O4 C43 C44 132.5(4) . .
O4 C43 C40 115.9(3) . .
C44 C43 C40 111.6(3) . .
C43 C44 C45 106.6(3) . .
C43 C44 H44 126.7 . .
C45 C44 H44 126.7 . .
N5 C45 C46 124.9(3) . .
N5 C45 C44 110.2(3) . .
C46 C45 C44 124.9(3) . .
N6 C46 C47 107.8(4) . .
N6 C46 C45 123.6(3) . .
C47 C46 C45 128.3(4) . .
C46 C47 C48 107.2(4) . .
C46 C47 H47 126.4 . .
C48 C47 H47 126.4 . .
C49 C48 C47 107.3(4) . .
C49 C48 H48 126.3 . .
C47 C48 H48 126.3 . .
N6 C49 C48 109.2(4) . .
N6 C49 H49 125.4 . .
C48 C49 H49 125.4 . .
O4 C50 H50A 109.5 . .
O4 C50 H50B 109.5 . .
H50A C50 H50B 109.5 . .
O4 C50 H50C 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
C3S C1S C1S 118.6(15) . 2_656
C3S C1S H1S1 107.7 . .
C1S C1S H1S1 107.7 2_656 .
C3S C1S H1S2 107.7 . .
C1S C1S H1S2 107.7 2_656 .
H1S1 C1S H1S2 107.1 . .
C3S C2S H2S1 109.5 . .
C3S C2S H2S2 109.5 . .
H2S1 C2S H2S2 109.5 . .
C3S C2S H2S3 109.5 . .
H2S1 C2S H2S3 109.5 . .
H2S2 C2S H2S3 109.5 . .
C1S C3S C2S 109.5(12) . .
C1S C3S H3S1 109.8 . .
C2S C3S H3S1 109.8 . .
C1S C3S H3S2 109.8 . .
C2S C3S H3S2 109.8 . .
H3S1 C3S H3S2 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C15 1.408(4) .
O1 C14 1.450(5) .
O2 C18 1.327(5) .
O2 C25 1.448(5) .
N1 C4 1.371(5) .
N1 C1 1.374(5) .
N1 H1 0.8600 .
N2 C20 1.324(5) .
N2 C15 1.467(5) .
N2 H2 0.8600 .
N3 C24 1.344(5) .
N3 C21 1.380(5) .
N3 H3 0.8600 .
C1 C2 1.371(5) .
C1 C16 1.489(5) .
C2 C3 1.419(6) .
C2 H2 0.9300 .
C3 C4 1.370(6) .
C3 H3 0.9300 .
C4 C5 1.495(6) .
C5 C6 1.542(7) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.515(7) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.502(8) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.543(7) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.512(7) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.540(6) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.545(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.525(6) .
C12 C16 1.544(5) .
C12 H12 0.9800 .
C13 C14 1.521(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C17 1.512(6) .
C14 H14 0.9800 .
C15 C18 1.508(5) .
C15 C16 1.552(5) .
C16 H16 0.9800 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 C19 1.348(5) .
C19 C20 1.444(5) .
C19 H19 0.9300 .
C20 C21 1.407(5) .
C21 C22 1.399(5) .
C22 C23 1.384(6) .
C22 H22 0.9300 .
C23 C24 1.386(6) .
C23 H23 0.9300 .
C24 H24 0.9300 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
O3 C40 1.406(4) .
O3 C39 1.454(4) .
O4 C43 1.317(5) .
O4 C50 1.443(5) .
N4 C26 1.379(5) .
N4 C29 1.386(5) .
N4 H4 0.8600 .
N5 C45 1.337(5) .
N5 C40 1.466(5) .
N5 H5 0.8600 .
N6 C49 1.351(5) .
N6 C46 1.379(5) .
N6 H6A 0.8600 .
C26 C27 1.362(5) .
C26 C41 1.504(5) .
C27 C28 1.431(5) .
C27 H27 0.9300 .
C28 C29 1.372(5) .
C28 H28 0.9300 .
C29 C30 1.492(5) .
C30 C31 1.533(6) .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C31 C32 1.526(6) .
C31 H31A 0.9700 .
C31 H31B 0.9700 .
C32 C33A 1.48(3) .
C32 C33 1.486(7) .
C32 H32A 0.9700 .
C32 H32B 0.9700 .
C32 H32C 0.9700 .
C32 H32D 0.9700 .
C33 C34 1.539(7) .
C33 H33A 0.9700 .
C33 H33B 0.9700 .
C33A C34 1.45(3) .
C33A H33C 0.9700 .
C33A H33D 0.9700 .
C34 C35 1.523(7) .
C34 C35A 1.54(3) .
C34 H34A 0.9700 .
C34 H34B 0.9700 .
C34 H34C 0.9700 .
C34 H34D 0.9700 .
C35 C36 1.510(6) .
C35 H35A 0.9700 .
C35 H35B 0.9700 .
C35A C36 1.37(3) .
C35A H35C 0.9700 .
C35A H35D 0.9700 .
C36 C37 1.545(5) .
C36 H36A 0.9700 .
C36 H36B 0.9700 .
C36 H36C 0.9700 .
C36 H36D 0.9700 .
C37 C38 1.524(5) .
C37 C41 1.538(5) .
C37 H37 0.9800 .
C38 C39 1.521(5) .
C38 H38A 0.9700 .
C38 H38B 0.9700 .
C39 C42 1.508(6) .
C39 H39 0.9800 .
C40 C43 1.510(5) .
C40 C41 1.549(5) .
C41 H41 0.9800 .
C42 H42A 0.9600 .
C42 H42B 0.9600 .
C42 H42C 0.9600 .
C43 C44 1.351(5) .
C44 C45 1.438(5) .
C44 H44 0.9300 .
C45 C46 1.409(5) .
C46 C47 1.388(6) .
C47 C48 1.395(6) .
C47 H47 0.9300 .
C48 C49 1.376(6) .
C48 H48 0.9300 .
C49 H49 0.9300 .
C50 H50A 0.9600 .
C50 H50B 0.9600 .
C50 H50C 0.9600 .
C1S C3S 1.452(14) .
C1S C1S 1.48(2) 2_656
C1S H1S1 0.9700 .
C1S H1S2 0.9700 .
C2S C3S 1.497(17) .
C2S H2S1 0.9600 .
C2S H2S2 0.9600 .
C2S H2S3 0.9600 .
C3S H3S1 0.9700 .
C3S H3S2 0.9700 .
