#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024768.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_4024768
loop_
_publ_author_name
'John R. Goodell'
'Jonathan P. McMullen'
'Nikolay Zaborenko'
'Jason R. Maloney'
'Chuan-Xing Ho'
'Klavs F. Jensen'
'John A. Porco'
'Aaron B. Beeler'
_publ_section_title
;
Development of an Automated Microfluidic Reaction Platform for
Multidimensional Screening: Reaction Discovery Employing
Bicyclo[3.2.1]octanoid Scaffolds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6169
_journal_page_last               6180
_journal_paper_doi               10.1021/jo901073v
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_weight         256.29
_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   difmap
_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                   7.5607(3)
_cell_length_b                   10.2164(5)
_cell_length_c                   17.0611(8)
_cell_measurement_reflns_used    8110
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.24
_cell_measurement_theta_min      2.39
_cell_volume                     1317.85(10)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13655
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(11)
_refine_ls_extinction_method     refall
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         1887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.2127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                1811
_reflns_number_total             1887
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901073v_si_005.cif
_cod_data_source_block           porco77
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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      P2(1)2(1)2(1)
_cod_database_code               4024768
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60462(12) 0.46988(10) 0.06380(6) 0.0348(2) Uani 1 1 d . . .
O2 O 0.78632(12) 0.24839(9) 0.08274(5) 0.0307(2) Uani 1 1 d . . .
O3 O 1.07243(13) 0.62383(10) -0.05022(5) 0.0321(2) Uani 1 1 d . . .
C1 C 0.76482(15) 0.47708(13) 0.06599(6) 0.0240(2) Uani 1 1 d . . .
C2 C 0.87992(16) 0.36101(12) 0.07518(6) 0.0229(2) Uani 1 1 d . . .
C3 C 1.05687(15) 0.37311(12) 0.07445(6) 0.0226(2) Uani 1 1 d . . .
H3 H 1.127(2) 0.3009(15) 0.0771(9) 0.032(4) Uiso 1 1 d . . .
C4 C 1.14412(14) 0.50578(12) 0.07075(7) 0.0220(2) Uani 1 1 d . . .
H4 H 1.270(2) 0.5026(16) 0.0543(9) 0.028(4) Uiso 1 1 d . . .
C5 C 1.03332(16) 0.58430(12) 0.01364(7) 0.0234(2) Uani 1 1 d . . .
C6 C 0.86037(16) 0.60744(12) 0.05788(6) 0.0232(2) Uani 1 1 d . . .
H6 H 0.786(2) 0.6719(16) 0.0328(9) 0.035(4) Uiso 1 1 d . . .
C7 C 0.93882(15) 0.65760(11) 0.13742(6) 0.0214(2) Uani 1 1 d . . .
H7 H 0.972(2) 0.7523(14) 0.1270(9) 0.029(4) Uiso 1 1 d . . .
C8 C 1.11651(15) 0.58162(11) 0.14908(6) 0.0213(2) Uani 1 1 d . . .
H8 H 1.1032(18) 0.5194(13) 0.1913(7) 0.016(3) Uiso 1 1 d . . .
C9 C 1.27009(18) 0.67304(14) 0.16707(9) 0.0331(3) Uani 1 1 d . . .
H9C H 1.384(2) 0.6275(16) 0.1770(10) 0.042(5) Uiso 1 1 d . . .
H9B H 1.285(2) 0.7323(17) 0.1229(11) 0.046(5) Uiso 1 1 d . . .
H9A H 1.243(2) 0.7264(17) 0.2150(10) 0.041(5) Uiso 1 1 d . . .
C10 C 0.8873(2) 0.13323(13) 0.09940(9) 0.0351(3) Uani 1 1 d . . .
H10C H 0.963(2) 0.1433(16) 0.1484(9) 0.035(4) Uiso 1 1 d . . .
H10B H 0.804(2) 0.0640(15) 0.1026(10) 0.034(4) Uiso 1 1 d . . .
H10A H 0.964(3) 0.1122(18) 0.0542(10) 0.048(5) Uiso 1 1 d . . .
C11 C 0.81326(15) 0.65710(12) 0.20625(6) 0.0215(2) Uani 1 1 d . . .
C12 C 0.77450(17) 0.54324(12) 0.24763(7) 0.0264(3) Uani 1 1 d . . .
H12 H 0.826(2) 0.4575(15) 0.2309(9) 0.029(4) Uiso 1 1 d . . .
C13 C 0.66106(19) 0.54641(14) 0.31221(8) 0.0315(3) Uani 1 1 d . . .
H13 H 0.638(2) 0.4636(16) 0.3397(10) 0.038(4) Uiso 1 1 d . . .
C14 C 0.58698(16) 0.66364(15) 0.33612(7) 0.0307(3) Uani 1 1 d . . .
H14 H 0.512(2) 0.6652(17) 0.3815(9) 0.039(4) Uiso 1 1 d . . .
C15 C 0.62129(17) 0.77685(13) 0.29465(8) 0.0291(3) Uani 1 1 d . . .
H15 H 0.570(2) 0.8587(16) 0.3096(9) 0.039(4) Uiso 1 1 d . . .
C16 C 0.73384(16) 0.77372(12) 0.22988(7) 0.0248(2) Uani 1 1 d . . .
H16 H 0.7570(19) 0.8496(14) 0.2012(8) 0.022(3) Uiso 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'
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
_geom_angle_publ_flag
C2 O2 C10 115.97(10) . . ?
O1 C1 C2 122.79(12) . . ?
O1 C1 C6 121.60(12) . . ?
C2 C1 C6 115.60(9) . . ?
C3 C2 O2 126.74(11) . . ?
C3 C2 C1 120.73(11) . . ?
O2 C2 C1 112.52(10) . . ?
C2 C3 C4 121.22(11) . . ?
C3 C4 C5 105.12(9) . . ?
C3 C4 C8 110.62(9) . . ?
C5 C4 C8 102.37(9) . . ?
O3 C5 C4 128.79(11) . . ?
O3 C5 C6 127.43(11) . . ?
C4 C5 C6 103.73(9) . . ?
C1 C6 C5 108.41(10) . . ?
C1 C6 C7 112.78(9) . . ?
C5 C6 C7 98.88(9) . . ?
C11 C7 C8 116.06(9) . . ?
C11 C7 C6 115.74(9) . . ?
C8 C7 C6 105.84(9) . . ?
C9 C8 C4 112.07(10) . . ?
C9 C8 C7 112.12(10) . . ?
C4 C8 C7 104.63(9) . . ?
C12 C11 C16 118.49(10) . . ?
C12 C11 C7 121.98(10) . . ?
C16 C11 C7 119.54(10) . . ?
C11 C12 C13 120.67(12) . . ?
C14 C13 C12 120.08(12) . . ?
C15 C14 C13 119.86(11) . . ?
C14 C15 C16 120.10(12) . . ?
C11 C16 C15 120.77(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2140(15) . ?
O2 C2 1.3569(14) . ?
O2 C10 1.4310(17) . ?
O3 C5 1.1990(14) . ?
C1 C2 1.4792(17) . ?
C1 C6 1.5215(18) . ?
C2 C3 1.3436(16) . ?
C3 C4 1.5088(16) . ?
C4 C5 1.5149(16) . ?
C4 C8 1.5588(16) . ?
C5 C6 1.5283(16) . ?
C6 C7 1.5671(16) . ?
C7 C11 1.5101(16) . ?
C7 C8 1.5643(16) . ?
C8 C9 1.5215(17) . ?
C11 C12 1.3919(17) . ?
C11 C16 1.3937(16) . ?
C12 C13 1.3966(18) . ?
C13 C14 1.384(2) . ?
C14 C15 1.380(2) . ?
C15 C16 1.3950(18) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659023
