#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029830.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_4029830
loop_
_publ_author_name
'Ding, Haixin'
'Li, Wei'
'Ruan, Zhizhong'
'Yang, Ruchun'
'Mao, Zhijie'
'Xiao, Qiang'
'Wu, Jun'
_publ_section_title
;
 Concise total synthesis of two marine natural nucleosides: trachycladines
 A and B.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1681
_journal_page_last               1685
_journal_paper_doi               10.3762/bjoc.10.176
_journal_volume                  10
_journal_year                    2014
_chemical_formula_sum            'C14 H16 Cl2 O3'
_chemical_formula_weight         303.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2508(5)
_cell_length_b                   14.2668(12)
_cell_length_c                   19.7267(13)
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6773
_cell_measurement_theta_min      2.8497
_cell_volume                     1477.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8650
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9913
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     432
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0548
_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)+(0.1608P)²+0.9020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1984
_reflns_number_gt                1915
_reflns_number_total             2612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-176-S2.cif
_cod_data_source_block           liu20120430e
_cod_depositor_comments          'Adding full bibliography for 4029830.cif.'
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4029830
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.3563(4) 1.25409(13) -0.14511(11) 0.1020(7) Uani 1 1 d U
Cl2 Cl 0.7226(4) 0.96780(13) -0.19877(7) 0.0956(7) Uani 1 1 d U
O1 O 0.3533(8) 0.8912(3) 0.17068(17) 0.0617(8) Uani 1 1 d U
O2 O 0.3588(7) 0.7900(3) 0.00531(19) 0.0640(9) Uani 1 1 d U
H2 H 0.2331 0.7663 -0.0124 0.096 Uiso 1 1 calc R
O3 O 0.6233(7) 0.7785(3) 0.12292(18) 0.0626(8) Uani 1 1 d U
C1 C 1.1382(12) 1.1716(4) -0.1168(3) 0.0637(10) Uani 1 1 d U
C2 C 1.0322(12) 1.1098(4) -0.1629(3) 0.0632(10) Uani 1 1 d U
H2A H 1.0751 1.1128 -0.2086 0.076 Uiso 1 1 calc R
C3 C 0.8620(11) 1.0437(4) -0.1397(3) 0.0595(9) Uani 1 1 d U
C4 C 0.7954(11) 1.0350(4) -0.0715(2) 0.0559(9) Uani 1 1 d U
C5 C 0.9020(11) 1.0996(4) -0.0278(3) 0.0584(9) Uani 1 1 d U
H5 H 0.8578 1.0975 0.0179 0.070 Uiso 1 1 calc R
C6 C 1.0718(12) 1.1674(4) -0.0494(3) 0.0637(10) Uani 1 1 d U
H6 H 1.1407 1.2097 -0.0186 0.076 Uiso 1 1 calc R
C7 C 0.6146(12) 0.9594(4) -0.0480(3) 0.0624(9) Uani 1 1 d U
H7 H 0.5113 0.9231 -0.0759 0.075 Uiso 1 1 calc R
O4 O 0.6286(7) 0.9530(3) 0.02451(16) 0.0590(7) Uani 1 1 d U
C9 C 0.3876(10) 0.9452(4) 0.0572(2) 0.0552(9) Uani 1 1 d U
H9 H 0.2637 0.9871 0.0358 0.066 Uiso 1 1 calc R
C10 C 0.2822(10) 0.8458(4) 0.0608(3) 0.0571(9) Uani 1 1 d U
H10 H 0.0958 0.8489 0.0614 0.069 Uiso 1 1 calc R
C11 C 0.3743(11) 0.8123(4) 0.1296(2) 0.0578(9) Uani 1 1 d U
H11 H 0.2626 0.7624 0.1465 0.069 Uiso 1 1 calc R
C12 C 0.4247(11) 0.9721(4) 0.1322(2) 0.0587(9) Uani 1 1 d U
H12 H 0.6049 0.9861 0.1403 0.070 Uiso 1 1 calc R
C13 C 0.2654(14) 1.0538(4) 0.1553(3) 0.0784(14) Uani 1 1 d U
H13A H 0.2854 1.0620 0.2033 0.118 Uiso 1 1 calc R
H13B H 0.0896 1.0418 0.1452 0.118 Uiso 1 1 calc R
H13C H 0.3195 1.1095 0.1322 0.118 Uiso 1 1 calc R
C14 C 0.7209(13) 0.7401(5) 0.1845(3) 0.0872(17) Uani 1 1 d U
H14A H 0.5832 0.7150 0.2108 0.131 Uiso 1 1 calc R
H14B H 0.8051 0.7885 0.2098 0.131 Uiso 1 1 calc R
H14C H 0.8401 0.6911 0.1742 0.131 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 0.0033 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'
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
C11 O1 C12 108.8(4)
C11 O3 C14 112.8(4)
C2 C1 C6 120.3(5)
C2 C1 Cl1 119.1(4)
C6 C1 Cl1 120.6(4)
C1 C2 C3 118.7(5)
C4 C3 C2 122.9(5)
C4 C3 Cl2 118.8(4)
C2 C3 Cl2 118.3(4)
C5 C4 C3 116.2(5)
C5 C4 C7 122.7(4)
C3 C4 C7 121.2(4)
C6 C5 C4 122.4(5)
C5 C6 C1 119.5(5)
O4 C7 C4 108.6(4)
C9 O4 C7 114.3(4)
O4 C9 C10 114.6(4)
O4 C9 C12 107.6(4)
C10 C9 C12 103.5(4)
O2 C10 C9 112.6(4)
O2 C10 C11 115.2(4)
C9 C10 C11 102.6(4)
O1 C11 O3 114.0(5)
O1 C11 C10 103.9(4)
O3 C11 C10 108.8(4)
O1 C12 C13 108.5(5)
O1 C12 C9 106.0(4)
C13 C12 C9 114.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.734(6)
Cl2 C3 1.750(5)
O1 C11 1.392(6)
O1 C12 1.431(6)
O2 C10 1.411(6)
O3 C11 1.399(7)
O3 C14 1.427(7)
C1 C2 1.384(8)
C1 C6 1.376(8)
C2 C3 1.377(8)
C3 C4 1.396(7)
C4 C5 1.382(7)
C4 C7 1.509(8)
C5 C6 1.383(8)
C7 O4 1.436(6)
O4 C9 1.425(7)
C9 C10 1.524(7)
C9 C12 1.541(7)
C10 C11 1.518(7)
C12 C13 1.505(8)
