#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:18:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178379 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/01/4020143.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_4020143
loop_
_publ_author_name
'Michael J. Marsella'
'Kunsang Yoon'
'Samia Estassi'
'Fook S. Tham'
'Dan B. Borchardt'
'Binh H. Bui'
'Peter R. Schreiner'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1881
_journal_page_last               1884
_journal_paper_doi               10.1021/jo0485132
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C53 H46'
_chemical_formula_weight         682.90
_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                 106.831(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.469(3)
_cell_length_b                   9.1484(16)
_cell_length_c                   25.911(4)
_cell_measurement_temperature    223(2)
_cell_volume                     3736.6(11)
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20494
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.29
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.11
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6365
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0623
_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)+(0.0962P)²+1.9164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1788
_reflns_number_gt                4586
_reflns_number_total             6365
_reflns_threshold_expression     >2sigma(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               4020143
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31776(18) 0.4046(3) 0.46757(11) 0.0453(7) Uani 1 1 d . . .
H1 H 0.3450 0.4434 0.4434 0.054 Uiso 1 1 calc R . .
C2 C 0.3457(2) 0.2762(4) 0.49279(14) 0.0638(9) Uani 1 1 d . . .
H2 H 0.3916 0.2275 0.4858 0.077 Uiso 1 1 calc R . .
C3 C 0.3067(3) 0.2165(4) 0.52889(16) 0.0760(11) Uani 1 1 d . . .
H3 H 0.3252 0.1259 0.5452 0.091 Uiso 1 1 calc R . .
C4 C 0.2426(3) 0.2870(4) 0.54075(13) 0.0674(10) Uani 1 1 d . . .
H4 H 0.2178 0.2458 0.5658 0.081 Uiso 1 1 calc R . .
C4A C 0.2111(2) 0.4246(3) 0.51573(11) 0.0478(7) Uani 1 1 d . . .
C5 C 0.0408(2) 0.6992(4) 0.50912(15) 0.0648(10) Uani 1 1 d . . .
H5 H 0.0165 0.6614 0.5350 0.078 Uiso 1 1 calc R . .
C6 C 0.0077(2) 0.8213(5) 0.48149(16) 0.0715(11) Uani 1 1 d . . .
H6 H -0.0408 0.8647 0.4871 0.086 Uiso 1 1 calc R . .
C7 C 0.0459(2) 0.8842(4) 0.44414(14) 0.0621(9) Uani 1 1 d . . .
H7 H 0.0240 0.9713 0.4262 0.075 Uiso 1 1 calc R . .
C8 C 0.11367(19) 0.8193(3) 0.43432(12) 0.0460(7) Uani 1 1 d . . .
H8 H 0.1387 0.8626 0.4098 0.055 Uiso 1 1 calc R . .
C8A C 0.14798(17) 0.6860(3) 0.46060(10) 0.0390(6) Uani 1 1 d . . .
C9 C 0.1442(2) 0.4981(4) 0.52640(11) 0.0550(9) Uani 1 1 d . . .
H9 H 0.1202 0.4598 0.5523 0.066 Uiso 1 1 calc R . .
C9A C 0.11148(19) 0.6274(4) 0.49981(11) 0.0485(8) Uani 1 1 d . . .
C10 C 0.21450(16) 0.6109(3) 0.44818(10) 0.0330(6) Uani 1 1 d . . .
C10A C 0.24845(17) 0.4819(3) 0.47681(10) 0.0383(6) Uani 1 1 d . . .
C11 C 0.24292(15) 0.6572(2) 0.40155(9) 0.0289(5) Uani 1 1 d . . .
C12 C 0.30616(15) 0.7470(2) 0.39984(9) 0.0289(5) Uani 1 1 d . . .
C13 C 0.37070(16) 0.8416(3) 0.43827(10) 0.0341(6) Uani 1 1 d . . .
H13A H 0.4077 0.7838 0.4676 0.041 Uiso 1 1 calc R . .
H13B H 0.3435 0.9188 0.4536 0.041 Uiso 1 1 calc R . .
C14 C 0.41911(15) 0.9041(2) 0.40185(9) 0.0288(5) Uani 1 1 d . . .
C15 C 0.48878(15) 0.9962(3) 0.41602(10) 0.0318(6) Uani 1 1 d . . .
H15 H 0.5084 1.0307 0.4516 0.038 Uiso 1 1 calc R . .
C16 C 0.53066(15) 1.0391(3) 0.37868(10) 0.0326(6) Uani 1 1 d . A .
C17 C 0.50142(15) 0.9851(2) 0.32566(10) 0.0320(6) Uani 1 1 d . A .
C18 C 0.42952(15) 0.8955(2) 0.31122(10) 0.0306(5) Uani 1 1 d . . .
H18 H 0.4093 0.8617 0.2755 0.037 Uiso 1 1 calc R . .
C19 C 0.38712(14) 0.8550(2) 0.34828(9) 0.0273(5) Uani 1 1 d . . .
C20 C 0.31335(14) 0.7601(2) 0.34534(9) 0.0265(5) Uani 1 1 d . . .
C21 C 0.25160(15) 0.6812(2) 0.31044(9) 0.0271(5) Uani 1 1 d . . .
C22 C 0.22727(15) 0.6753(3) 0.25146(9) 0.0290(5) Uani 1 1 d . . .
C23 C 0.18318(17) 0.5574(3) 0.22234(11) 0.0404(6) Uani 1 1 d . . .
H23 H 0.1701 0.4772 0.2412 0.048 Uiso 1 1 calc R . .
C24 C 0.1583(2) 0.5550(3) 0.16727(11) 0.0511(8) Uani 1 1 d . . .
H24 H 0.1293 0.4732 0.1489 0.061 Uiso 1 1 calc R . .
C25 C 0.17552(19) 0.6717(4) 0.13834(11) 0.0506(8) Uani 1 1 d . . .
H25 H 0.1590 0.6697 0.1004 0.061 Uiso 1 1 calc R . .
C26 C 0.21737(18) 0.7911(3) 0.16602(11) 0.0455(7) Uani 1 1 d . . .
H26 H 0.2292 0.8715 0.1468 0.055 Uiso 1 1 calc R . .
C27 C 0.24207(16) 0.7942(3) 0.22139(10) 0.0369(6) Uani 1 1 d . . .
H27 H 0.2694 0.8777 0.2394 0.044 Uiso 1 1 calc R . .
C28 C 0.60591(17) 1.1414(3) 0.39670(12) 0.0410(6) Uani 1 1 d D . .
H28A H 0.6504 1.1077 0.3813 0.049 Uiso 0.933(4) 1 calc PR A 3
H28B H 0.6286 1.1360 0.4360 0.049 Uiso 0.933(4) 1 calc PR A 3
H28C H 0.6312 1.1528 0.3670 0.049 Uiso 0.067(4) 1 calc PR A 4
H28D H 0.6486 1.0961 0.4269 0.049 Uiso 0.067(4) 1 calc PR A 4
C29 C 0.5851(2) 1.3021(3) 0.38037(14) 0.0441(8) Uani 0.933(4) 1 d PD A 3
H29A H 0.6382 1.3574 0.3881 0.053 Uiso 0.933(4) 1 calc PR A 3
H29B H 0.5578 1.3066 0.3414 0.053 Uiso 0.933(4) 1 calc PR A 3
C30 C 0.5280(2) 1.3739(3) 0.40876(14) 0.0490(9) Uani 0.933(4) 1 d PD A 3
H30A H 0.5555 1.3716 0.4477 0.059 Uiso 0.933(4) 1 calc PR A 3
H30B H 0.4750 1.3184 0.4015 0.059 Uiso 0.933(4) 1 calc PR A 3
C31 C 0.5076(3) 1.5322(4) 0.39094(18) 0.0622(11) Uani 0.933(4) 1 d PD A 3
H31A H 0.5595 1.5890 0.4000 0.093 Uiso 0.933(4) 1 calc PR A 3
H31B H 0.4689 1.5727 0.4092 0.093 Uiso 0.933(4) 1 calc PR A 3
H31C H 0.4813 1.5353 0.3523 0.093 Uiso 0.933(4) 1 calc PR A 3
C29D C 0.585(3) 1.295(2) 0.4143(15) 0.0441(8) Uani 0.067(4) 1 d PD A 4
H29C H 0.5469 1.2844 0.4373 0.053 Uiso 0.067(4) 1 calc PR A 4
H29D H 0.6369 1.3422 0.4357 0.053 Uiso 0.067(4) 1 calc PR A 4
C30D C 0.542(3) 1.391(4) 0.3666(15) 0.0490(9) Uani 0.067(4) 1 d PD A 4
H30C H 0.4825 1.3619 0.3517 0.059 Uiso 0.067(4) 1 calc PR A 4
H30D H 0.5703 1.3795 0.3384 0.059 Uiso 0.067(4) 1 calc PR A 4
C31D C 0.547(4) 1.552(3) 0.385(2) 0.0622(11) Uani 0.067(4) 1 d PD A 4
H31D H 0.5024 1.6076 0.3604 0.093 Uiso 0.067(4) 1 calc PR A 4
H31E H 0.6018 1.5919 0.3858 0.093 Uiso 0.067(4) 1 calc PR A 4
H31F H 0.5402 1.5567 0.4211 0.093 Uiso 0.067(4) 1 calc PR A 4
C32 C 0.54709(17) 1.0122(3) 0.28376(11) 0.0395(6) Uani 1 1 d D . .
H32A H 0.5893 1.0896 0.2965 0.047 Uiso 0.872(8) 1 calc PR B 1
H32B H 0.5062 1.0462 0.2504 0.047 Uiso 0.872(8) 1 calc PR B 1
H32C H 0.5612 1.1161 0.2829 0.047 Uiso 0.128(8) 1 d PR B 2
H32D H 0.5110 0.9840 0.2480 0.047 Uiso 0.128(8) 1 d PR B 2
C33 C 0.5917(2) 0.8741(4) 0.27170(15) 0.0394(10) Uani 0.872(8) 1 d PD B 1
H33A H 0.5487 0.7999 0.2561 0.047 Uiso 0.872(8) 1 calc PR B 1
H33B H 0.6207 0.8980 0.2447 0.047 Uiso 0.872(8) 1 calc PR B 1
C34 C 0.6551(2) 0.8104(4) 0.32032(15) 0.0482(11) Uani 0.872(8) 1 d PD B 1
H34A H 0.6265 0.7884 0.3478 0.058 Uiso 0.872(8) 1 calc PR B 1
H34B H 0.6992 0.8832 0.3354 0.058 Uiso 0.872(8) 1 calc PR B 1
C35 C 0.6963(2) 0.6724(4) 0.30761(15) 0.0690(10) Uani 0.872(8) 1 d PRD B 1
H35A H 0.6531 0.5989 0.2936 0.103 Uiso 0.872(8) 1 calc PR B 1
H35B H 0.7368 0.6363 0.3402 0.103 Uiso 0.872(8) 1 calc PR B 1
H35C H 0.7254 0.6938 0.2809 0.103 Uiso 0.872(8) 1 calc PR B 1
C33D C 0.6278(11) 0.919(2) 0.2994(12) 0.069(10) Uani 0.128(8) 1 d PD B 2
H33C H 0.6657 0.9495 0.2785 0.083 Uiso 0.128(8) 1 calc PR B 2
H33D H 0.6576 0.9330 0.3377 0.083 Uiso 0.128(8) 1 calc PR B 2
C34D C 0.6060(15) 0.761(3) 0.2890(12) 0.069(10) Uani 0.128(8) 1 d PD B 2
H34C H 0.5751 0.7458 0.2509 0.082 Uiso 0.128(8) 1 calc PR B 2
H34D H 0.5701 0.7279 0.3110 0.082 Uiso 0.128(8) 1 calc PR B 2
C35D C 0.6898(19) 0.675(3) 0.3038(16) 0.0690(10) Uani 0.128(8) 1 d PD B 2
H35D H 0.6941 0.6199 0.2726 0.103 Uiso 0.128(8) 1 calc PR B 2
H35E H 0.6911 0.6075 0.3330 0.103 Uiso 0.128(8) 1 calc PR B 2
H35F H 0.7371 0.7420 0.3151 0.103 Uiso 0.128(8) 1 calc PR B 2
C1' C 0.28386(16) 0.3717(3) 0.33549(10) 0.0337(6) Uani 1 1 d . . .
H1' H 0.3255 0.4329 0.3287 0.040 Uiso 1 1 calc R . .
C2' C 0.29635(18) 0.2207(3) 0.33758(11) 0.0415(6) Uani 1 1 d . . .
H2' H 0.3461 0.1801 0.3328 0.050 Uiso 1 1 calc R . .
C3' C 0.23421(18) 0.1320(3) 0.34680(12) 0.0475(7) Uani 1 1 d . . .
H3' H 0.2414 0.0300 0.3479 0.057 Uiso 1 1 calc R . .
C4' C 0.16237(18) 0.1910(3) 0.35430(12) 0.0446(7) Uani 1 1 d . . .
H4' H 0.1207 0.1287 0.3604 0.054 Uiso 1 1 calc R . .
C5' C 0.14951(16) 0.3430(3) 0.35306(10) 0.0336(6) Uani 1 1 d . . .
C6' C 0.07066(16) 0.4036(3) 0.36226(11) 0.0375(6) Uani 1 1 d . . .
H6'1 H 0.0796 0.4156 0.4011 0.045 Uiso 1 1 calc R . .
H6'2 H 0.0243 0.3336 0.3489 0.045 Uiso 1 1 calc R . .
C7' C 0.04517(15) 0.5490(3) 0.33461(10) 0.0328(6) Uani 1 1 d . . .
C8' C -0.03929(17) 0.5892(3) 0.31809(12) 0.0444(7) Uani 1 1 d . . .
H8' H -0.0803 0.5254 0.3242 0.053 Uiso 1 1 calc R . .
C9' C -0.06481(18) 0.7214(3) 0.29276(14) 0.0526(8) Uani 1 1 d . . .
H9' H -0.1225 0.7470 0.2814 0.063 Uiso 1 1 calc R . .
C10' C -0.00402(17) 0.8153(3) 0.28447(12) 0.0447(7) Uani 1 1 d . . .
H10' H -0.0204 0.9067 0.2682 0.054 Uiso 1 1 calc R . .
C11' C 0.07977(16) 0.7762(3) 0.29973(10) 0.0345(6) Uani 1 1 d . . .
H11' H 0.1201 0.8406 0.2931 0.041 Uiso 1 1 calc R . .
C12' C 0.10651(15) 0.6417(2) 0.32509(10) 0.0294(5) Uani 1 1 d . . .
C13' C 0.20055(15) 0.6012(2) 0.34331(9) 0.0272(5) Uani 1 1 d . . .
C14' C 0.21145(15) 0.4331(2) 0.34319(9) 0.0285(5) Uani 1 1 d . . .
