#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/42/1504216.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_1504216
loop_
_publ_author_name
'Krawczuk, Paul J.'
'Schöne, Niklas'
'Baran, Phil S.'
_publ_section_title
;
 A synthesis of the carbon skeleton of maoecrystal V.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4774
_journal_page_last               4776
_journal_paper_doi               10.1021/ol901963v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C21 H24 O6'
_chemical_formula_weight         372.40
_chemical_name_common            PK-IV-261
_chemical_name_systematic
;
 ?
;
_space_group.centring_type       P
_space_group_IT_number           14
_space_group.IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.941(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1446(2)
_cell_length_b                   10.9191(3)
_cell_length_c                   23.7565(7)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.72
_cell_volume                     1852.24(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26439
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         3.72
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.9685
_exptl_absorpt_correction_T_min  0.9096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00126(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0333
_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)+(0.0373P)²+0.7638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                2908
_reflns_number_total             3393
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901963v_si_004.cif
_cod_data_source_block           baran41
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1504216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.63015(18) 0.24621(12) 0.37158(5) 0.0177(3) Uani 1 1 d .
C2 C 0.64616(19) 0.13007(12) 0.40908(6) 0.0213(3) Uani 1 1 d .
C3 C 0.7115(2) 0.17100(13) 0.46884(6) 0.0245(3) Uani 1 1 d .
H3 H 0.7090 0.1013 0.4961 0.029 Uiso 1 1 calc R
C4 C 0.9068(2) 0.22989(13) 0.46786(6) 0.0257(3) Uani 1 1 d .
H4A H 1.0017 0.1669 0.4597 0.031 Uiso 1 1 calc R
H4B H 0.9393 0.2664 0.5051 0.031 Uiso 1 1 calc R
C5 C 0.90601(19) 0.33002(12) 0.42204(5) 0.0205(3) Uani 1 1 d .
H5 H 0.9672 0.2923 0.3890 0.025 Uiso 1 1 calc R
C6 C 1.02508(19) 0.43910(13) 0.43846(5) 0.0222(3) Uani 1 1 d .
C7 C 0.79779(19) 0.57883(12) 0.39617(6) 0.0218(3) Uani 1 1 d .
H7A H 0.8001 0.6531 0.3723 0.026 Uiso 1 1 calc R
H7B H 0.7266 0.5990 0.4300 0.026 Uiso 1 1 calc R
C8 C 0.69387(18) 0.47698(12) 0.36343(5) 0.0181(3) Uani 1 1 d .
C9 C 0.79671(19) 0.45807(12) 0.30814(5) 0.0197(3) Uani 1 1 d .
C10 C 0.7482(2) 0.54251(13) 0.26193(6) 0.0256(3) Uani 1 1 d .
H10 H 0.8271 0.5448 0.2305 0.031 Uiso 1 1 calc R
C11 C 0.6001(2) 0.61597(13) 0.26157(6) 0.0269(3) Uani 1 1 d .
H11 H 0.5827 0.6694 0.2303 0.032 Uiso 1 1 calc R
C12 C 0.4582(2) 0.62138(13) 0.30653(6) 0.0236(3) Uani 1 1 d .
C13 C 0.48955(19) 0.51725(12) 0.34989(6) 0.0211(3) Uani 1 1 d .
H13A H 0.4189 0.4446 0.3361 0.025 Uiso 1 1 calc R
H13B H 0.4337 0.5430 0.3856 0.025 Uiso 1 1 calc R
C14 C 0.70165(18) 0.36211(12) 0.40115(5) 0.0181(3) Uani 1 1 d .
C15 C 0.57760(19) 0.36912(13) 0.45196(5) 0.0221(3) Uani 1 1 d .
H15 H 0.5038 0.4392 0.4596 0.026 Uiso 1 1 calc R
C16 C 0.5793(2) 0.27108(13) 0.48489(6) 0.0259(3) Uani 1 1 d .
H16 H 0.5021 0.2646 0.5165 0.031 Uiso 1 1 calc R
C17 C 0.4615(2) 0.06128(13) 0.40651(6) 0.0278(3) Uani 1 1 d .
H17A H 0.4261 0.0433 0.3672 0.042 Uiso 1 1 calc R
H17B H 0.3642 0.1117 0.4232 0.042 Uiso 1 1 calc R
H17C H 0.4749 -0.0156 0.4276 0.042 Uiso 1 1 calc R
C18 C 0.8491(2) -0.04747(13) 0.40170(6) 0.0270(3) Uani 1 1 d .
C19 C 0.9966(2) -0.10098(14) 0.36586(8) 0.0363(4) Uani 1 1 d .
H19A H 1.0545 -0.1713 0.3852 0.054 Uiso 1 1 calc R
H19B H 1.0923 -0.0389 0.3590 0.054 Uiso 1 1 calc R
H19C H 0.9396 -0.1277 0.3298 0.054 Uiso 1 1 calc R
C20 C 0.4632(2) 0.74950(13) 0.33366(7) 0.0319(4) Uani 1 1 d .
H20A H 0.5870 0.7639 0.3514 0.048 Uiso 1 1 calc R
H20B H 0.3676 0.7545 0.3622 0.048 Uiso 1 1 calc R
H20C H 0.4379 0.8116 0.3046 0.048 Uiso 1 1 calc R
C21 C 0.2623(2) 0.60484(15) 0.27858(7) 0.0329(4) Uani 1 1 d .
H21A H 0.2384 0.6710 0.2514 0.049 Uiso 1 1 calc R
H21B H 0.1677 0.6072 0.3075 0.049 Uiso 1 1 calc R
H21C H 0.2561 0.5258 0.2591 0.049 Uiso 1 1 calc R
O1 O 0.56361(13) 0.24190(8) 0.32422(4) 0.0227(2) Uani 1 1 d .
O2 O 0.79151(13) 0.06183(8) 0.38058(4) 0.0219(2) Uani 1 1 d .
O3 O 1.16452(14) 0.43071(10) 0.46828(4) 0.0291(2) Uani 1 1 d .
O4 O 0.98764(13) 0.54848(9) 0.41373(4) 0.0238(2) Uani 1 1 d .
O5 O 0.92213(14) 0.38357(9) 0.30337(4) 0.0239(2) Uani 1 1 d .
O6 O 0.78827(16) -0.09472(10) 0.44303(5) 0.0356(3) Uani 1 1 d .
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'
O O 0.0492 0.0322 '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
O1 C1 C14 125.17(12)
O1 C1 C2 121.47(12)
C14 C1 C2 113.34(10)
O2 C2 C17 111.05(11)
O2 C2 C3 112.06(11)
C17 C2 C3 114.52(12)
O2 C2 C1 100.97(10)
C17 C2 C1 109.53(11)
C3 C2 C1 107.77(11)
C16 C3 C4 106.16(12)
C16 C3 C2 105.71(11)
C4 C3 C2 110.67(11)
C16 C3 H3 111.3
C4 C3 H3 111.3
C2 C3 H3 111.3
C3 C4 C5 109.00(11)
C3 C4 H4A 109.9
C5 C4 H4A 109.9
C3 C4 H4B 109.9
C5 C4 H4B 109.9
H4A C4 H4B 108.3
C6 C5 C4 112.89(11)
C6 C5 C14 114.66(11)
C4 C5 C14 111.30(11)
C6 C5 H5 105.7
C4 C5 H5 105.7
C14 C5 H5 105.7
O3 C6 O4 117.98(13)
O3 C6 C5 122.65(13)
O4 C6 C5 118.91(11)
O4 C7 C8 114.44(11)
O4 C7 H7A 108.7
C8 C7 H7A 108.7
O4 C7 H7B 108.7
C8 C7 H7B 108.7
H7A C7 H7B 107.6
C7 C8 C9 107.03(11)
C7 C8 C14 106.73(10)
C9 C8 C14 112.20(11)
C7 C8 C13 109.64(11)
C9 C8 C13 109.54(11)
C14 C8 C13 111.54(11)
O5 C9 C10 120.41(12)
O5 C9 C8 122.84(12)
C10 C9 C8 116.53(12)
C11 C10 C9 123.56(13)
C11 C10 H10 118.2
C9 C10 H10 118.2
C10 C11 C12 125.28(13)
C10 C11 H11 117.4
C12 C11 H11 117.4
C11 C12 C21 108.36(12)
C11 C12 C20 109.12(12)
C21 C12 C20 107.14(12)
C11 C12 C13 111.09(11)
C21 C12 C13 108.08(11)
C20 C12 C13 112.87(12)
C12 C13 C8 117.50(11)
C12 C13 H13A 107.9
C8 C13 H13A 107.9
C12 C13 H13B 107.9
C8 C13 H13B 107.9
H13A C13 H13B 107.2
C15 C14 C1 102.22(10)
C15 C14 C8 114.16(11)
C1 C14 C8 113.71(10)
C15 C14 C5 108.75(10)
C1 C14 C5 104.73(10)
C8 C14 C5 112.41(11)
C16 C15 C14 115.66(13)
C16 C15 H15 122.2
C14 C15 H15 122.2
C15 C16 C3 115.53(12)
C15 C16 H16 122.2
C3 C16 H16 122.2
C2 C17 H17A 109.5
C2 C17 H17B 109.5
H17A C17 H17B 109.5
C2 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O6 C18 O2 124.54(14)
O6 C18 C19 125.30(14)
O2 C18 C19 110.15(12)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C12 C20 H20A 109.5
C12 C20 H20B 109.5
H20A C20 H20B 109.5
C12 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C12 C21 H21A 109.5
C12 C21 H21B 109.5
H21A C21 H21B 109.5
C12 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C18 O2 C2 119.30(11)
C6 O4 C7 119.85(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2075(16)
C1 C14 1.5269(17)
C1 C2 1.5518(18)
C2 O2 1.4627(16)
C2 C17 1.518(2)
C2 C3 1.5454(18)
C3 C16 1.502(2)
C3 C4 1.537(2)
C3 H3 1.0000
C4 C5 1.5426(18)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5073(19)
C5 C14 1.5659(18)
C5 H5 1.0000
C6 O3 1.2062(17)
C6 O4 1.3536(17)
C7 O4 1.4441(16)
C7 C8 1.5343(17)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.5406(18)
C8 C14 1.5414(17)
C8 C13 1.5479(18)
C9 O5 1.2183(17)
C9 C10 1.4661(19)
C10 C11 1.328(2)
C10 H10 0.9500
C11 C12 1.498(2)
C11 H11 0.9500
C12 C21 1.540(2)
C12 C20 1.540(2)
C12 C13 1.5454(18)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.5234(18)
C15 C16 1.326(2)
C15 H15 0.9500
C16 H16 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 O6 1.2032(18)
C18 O2 1.3533(17)
C18 C19 1.496(2)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
