#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:54:59 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178923 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/52/4115292.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_4115292
loop_
_publ_author_name
'Ohyun Kwon'
'Seung Bum Park'
'Stuart L. Schreiber'
_publ_section_title
;
 Skeletal Diversity via a Branched Pathway: Efficient Synthesis of 29400
 Discrete, Polycyclic Compounds and Their Arraying into Stock Solutions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13402
_journal_page_last               13404
_journal_paper_doi               10.1021/ja028086e
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C23 H20 Cl2 O4'
_chemical_formula_weight         431.29
_chemical_name_systematic
; 

 ? 

;
_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                 95.5260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2454(5)
_cell_length_b                   8.6672(4)
_cell_length_c                   25.6417(15)
_cell_measurement_reflns_used    134
_cell_measurement_temperature    213(2)
_cell_volume                     2045.16(19)
_computing_cell_refinement       'SMART (BRUKER, V5.054, 1998)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.01, 1999)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 1998, V5.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_method       'ω, 0.3 deg'
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12796
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0709P)²+0.9201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                2992
_reflns_number_total             4409
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja028086e-2_s2_4.cif
_cod_data_source_block           sls56t
_cod_database_code               4115292
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
O1 O -0.57982(18) -0.86275(19) -0.22940(6) 0.0411(4) Uani 1 1 d .
O2 O -0.52170(18) -1.03621(19) -0.16719(6) 0.0407(4) Uani 1 1 d .
O3 O -0.6413(2) -0.6458(2) -0.27379(7) 0.0549(5) Uani 1 1 d .
O4 O 0.00697(17) -0.74715(17) -0.25140(6) 0.0362(4) Uani 1 1 d .
H4A H 0.0012 -0.6793 -0.2743 0.054 Uiso 1 1 calc R
C1 C -0.5639(2) -0.9088(3) -0.17789(8) 0.0334(5) Uani 1 1 d .
C2 C -0.5992(2) -0.7764(2) -0.14210(8) 0.0299(5) Uani 1 1 d .
C3 C -0.4504(2) -0.7040(2) -0.11868(8) 0.0287(5) Uani 1 1 d .
H3A H -0.4168 -0.7671 -0.0877 0.034 Uiso 1 1 calc R
C4 C -0.4767(2) -0.5433(2) -0.09838(9) 0.0327(5) Uani 1 1 d .
C5 C -0.5786(3) -0.4524(3) -0.12219(9) 0.0387(5) Uani 1 1 d .
H5A H -0.5888 -0.3533 -0.1081 0.046 Uiso 1 1 calc R
C6 C -0.6780(3) -0.4940(3) -0.16923(10) 0.0416(6) Uani 1 1 d .
H6A H -0.6467 -0.4392 -0.1996 0.050 Uiso 1 1 calc R
H6B H -0.7761 -0.4583 -0.1641 0.050 Uiso 1 1 calc R
C7 C -0.6839(2) -0.6675(3) -0.18137(9) 0.0353(5) Uani 1 1 d .
H7A H -0.7874 -0.6980 -0.1824 0.042 Uiso 1 1 calc R
C8 C -0.6346(3) -0.7121(3) -0.23314(9) 0.0402(6) Uani 1 1 d .
C9 C -0.3820(3) -0.4895(3) -0.05277(9) 0.0427(6) Uani 1 1 d .
H9A H -0.4024 -0.3913 -0.0397 0.051 Uiso 1 1 calc R
C10 C -0.2719(3) -0.5635(3) -0.02826(10) 0.0560(7) Uani 1 1 d .
H10A H -0.2466 -0.6621 -0.0397 0.067 Uiso 1 1 calc R
H10B H -0.2182 -0.5180 0.0007 0.067 Uiso 1 1 calc R
C11 C -0.3285(2) -0.7078(2) -0.15462(8) 0.0276(4) Uani 1 1 d .
C12 C -0.3174(2) -0.6023(2) -0.19511(8) 0.0302(5) Uani 1 1 d .
H12A H -0.3862 -0.5225 -0.2003 0.036 Uiso 1 1 calc R
C13 C -0.2071(2) -0.6127(3) -0.22785(8) 0.0315(5) Uani 1 1 d .
H13A H -0.2017 -0.5411 -0.2551 0.038 Uiso 1 1 calc R
C14 C -0.1043(2) -0.7295(2) -0.22025(8) 0.0290(5) Uani 1 1 d .
C15 C -0.1111(2) -0.8333(3) -0.17988(9) 0.0325(5) Uani 1 1 d .
H15A H -0.0409 -0.9114 -0.1743 0.039 Uiso 1 1 calc R
C16 C -0.2225(2) -0.8217(2) -0.14742(8) 0.0314(5) Uani 1 1 d .
H16A H -0.2264 -0.8927 -0.1199 0.038 Uiso 1 1 calc R
C17 C -0.6823(2) -0.8295(3) -0.09685(8) 0.0320(5) Uani 1 1 d .
C18 C -0.8050(3) -0.7517(3) -0.08370(10) 0.0419(6) Uani 1 1 d .
H18A H -0.8418 -0.6684 -0.1044 0.050 Uiso 1 1 calc R
C19 C -0.8740(3) -0.7958(4) -0.04016(11) 0.0531(7) Uani 1 1 d .
H19A H -0.9568 -0.7419 -0.0317 0.064 Uiso 1 1 calc R
C20 C -0.8221(3) -0.9174(4) -0.00950(10) 0.0551(8) Uani 1 1 d .
H20A H -0.8685 -0.9464 0.0200 0.066 Uiso 1 1 calc R
C21 C -0.7019(3) -0.9960(3) -0.02244(10) 0.0527(7) Uani 1 1 d .
H21A H -0.6668 -1.0802 -0.0019 0.063 Uiso 1 1 calc R
C22 C -0.6317(3) -0.9526(3) -0.06543(10) 0.0429(6) Uani 1 1 d .
H22A H -0.5488 -1.0070 -0.0735 0.052 Uiso 1 1 calc R
C1S C -0.0730(3) -0.3378(4) -0.13373(13) 0.0694(9) Uani 1 1 d .
H1SA H -0.0949 -0.4431 -0.1231 0.083 Uiso 1 1 calc R
H1SB H -0.0392 -0.3428 -0.1688 0.083 Uiso 1 1 calc R
Cl1 Cl -0.23053(8) -0.22811(8) -0.13656(3) 0.0557(2) Uani 1 1 d .
Cl2 Cl 0.06492(10) -0.26334(16) -0.09023(4) 0.1064(5) 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 0.0033 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
C1 O1 C8 109.95(18)
O2 C1 O1 119.5(2)
O2 C1 C2 129.9(2)
O1 C1 C2 110.52(19)
C17 C2 C1 112.59(18)
C17 C2 C7 114.94(18)
C1 C2 C7 101.14(17)
C17 C2 C3 108.39(16)
C1 C2 C3 107.42(17)
C7 C2 C3 112.04(18)
C4 C3 C11 112.36(17)
C4 C3 C2 109.50(17)
C11 C3 C2 115.47(17)
C5 C4 C9 121.3(2)
C5 C4 C3 121.1(2)
C9 C4 C3 117.5(2)
C4 C5 C6 125.7(2)
C5 C6 C7 114.15(19)
C8 C7 C6 115.2(2)
C8 C7 C2 104.03(19)
C6 C7 C2 117.53(19)
O3 C8 O1 120.0(2)
O3 C8 C7 131.3(3)
O1 C8 C7 108.64(19)
C10 C9 C4 127.1(2)
C16 C11 C12 117.58(19)
C16 C11 C3 119.20(18)
C12 C11 C3 123.22(19)
C13 C12 C11 121.3(2)
C12 C13 C14 119.77(19)
O4 C14 C15 117.20(19)
O4 C14 C13 122.76(19)
C15 C14 C13 120.0(2)
C14 C15 C16 119.6(2)
C15 C16 C11 121.7(2)
C22 C17 C18 118.0(2)
C22 C17 C2 120.5(2)
C18 C17 C2 121.5(2)
C17 C18 C19 120.7(3)
C20 C19 C18 120.5(3)
C19 C20 C21 119.3(2)
C20 C21 C22 120.7(3)
C21 C22 C17 120.8(3)
Cl2 C1S Cl1 112.65(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.374(3)
O1 C8 1.400(3)
O2 C1 1.194(3)
O3 C8 1.187(3)
O4 C14 1.370(3)
C1 C2 1.524(3)
C2 C17 1.523(3)
C2 C7 1.539(3)
C2 C3 1.578(3)
C3 C4 1.515(3)
C3 C11 1.523(3)
C4 C5 1.331(3)
C4 C9 1.468(3)
C5 C6 1.488(3)
C6 C7 1.535(3)
C7 C8 1.496(3)
C9 C10 1.312(4)
C11 C16 1.391(3)
C11 C12 1.395(3)
C12 C13 1.385(3)
C13 C14 1.389(3)
C14 C15 1.377(3)
C15 C16 1.389(3)
C17 C22 1.390(3)
C17 C18 1.389(3)
C18 C19 1.392(4)
C19 C20 1.374(4)
C20 C21 1.371(4)
C21 C22 1.384(4)
C1S Cl2 1.735(3)
C1S Cl1 1.735(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 O1 C1 O2 178.1(2)
C8 O1 C1 C2 -4.6(2)
O2 C1 C2 C17 -42.3(3)
O1 C1 C2 C17 140.81(18)
O2 C1 C2 C7 -165.5(2)
O1 C1 C2 C7 17.6(2)
O2 C1 C2 C3 76.9(3)
O1 C1 C2 C3 -99.9(2)
C17 C2 C3 C4 -77.2(2)
C1 C2 C3 C4 160.92(17)
C7 C2 C3 C4 50.7(2)
C17 C2 C3 C11 154.84(18)
C1 C2 C3 C11 32.9(2)
C7 C2 C3 C11 -77.3(2)
C11 C3 C4 C5 95.2(2)
C2 C3 C4 C5 -34.5(3)
C11 C3 C4 C9 -82.5(2)
C2 C3 C4 C9 147.75(19)
C9 C4 C5 C6 178.6(2)
C3 C4 C5 C6 1.0(4)
C4 C5 C6 C7 15.4(3)
C5 C6 C7 C8 -118.3(2)
C5 C6 C7 C2 4.9(3)
C17 C2 C7 C8 -144.39(19)
C1 C2 C7 C8 -22.8(2)
C3 C2 C7 C8 91.3(2)
C17 C2 C7 C6 87.0(2)
C1 C2 C7 C6 -151.5(2)
C3 C2 C7 C6 -37.3(3)
C1 O1 C8 O3 172.0(2)
C1 O1 C8 C7 -11.3(2)
C6 C7 C8 O3 -31.7(4)
C2 C7 C8 O3 -161.8(3)
C6 C7 C8 O1 152.05(19)
C2 C7 C8 O1 22.0(2)
C5 C4 C9 C10 -175.0(3)
C3 C4 C9 C10 2.7(4)
C4 C3 C11 C16 133.5(2)
C2 C3 C11 C16 -99.9(2)
C4 C3 C11 C12 -46.8(3)
C2 C3 C11 C12 79.8(2)
C16 C11 C12 C13 1.6(3)
C3 C11 C12 C13 -178.08(19)
C11 C12 C13 C14 -0.5(3)
C12 C13 C14 O4 179.52(19)
C12 C13 C14 C15 -0.8(3)
O4 C14 C15 C16 -179.35(19)
C13 C14 C15 C16 1.0(3)
C14 C15 C16 C11 0.2(3)
C12 C11 C16 C15 -1.4(3)
C3 C11 C16 C15 178.24(19)
C1 C2 C17 C22 50.8(3)
C7 C2 C17 C22 165.9(2)
C3 C2 C17 C22 -67.9(3)
C1 C2 C17 C18 -133.1(2)
C7 C2 C17 C18 -18.0(3)
C3 C2 C17 C18 108.2(2)
C22 C17 C18 C19 0.4(4)
C2 C17 C18 C19 -175.8(2)
C17 C18 C19 C20 -0.2(4)
C18 C19 C20 C21 -0.5(4)
C19 C20 C21 C22 0.9(4)
C20 C21 C22 C17 -0.7(4)
C18 C17 C22 C21 0.1(4)
C2 C17 C22 C21 176.3(2)
