#------------------------------------------------------------------------------
#$Date: 2016-03-05 10:04:17 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177674 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/83/7118375.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_7118375
loop_
_publ_author_name
'Yanai, Hikaru'
'Kobayashi, Osamu'
'Takada, Kenji'
'Isono, Takuya'
'Satoh, Toshifumi'
'Matsumoto, Takashi'
_publ_section_title
;
 Sequential Mukaiyama-Michael reaction induced by carbon acids.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3280
_journal_page_last               3283
_journal_paper_doi               10.1039/c5cc10115h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C20 H23 Br O5'
_chemical_formula_sum            'C20 H23 Br O5'
_chemical_formula_weight         423.29
_chemical_melting_point          84.0
_chemical_name_systematic
;
Ethyl 2-((3S*,4S*)-6-bromo-2-oxo-3-((R*)-3-oxocycloheptyl)chroman-4-yl)acetate
;
_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_date             'May 07 2015'
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0177(12)
_cell_length_b                   6.6196(6)
_cell_length_c                   23.898(2)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.99
_cell_volume                     1898.0(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8856
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    2.193
_exptl_absorpt_correction_T_max  0.8797
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0261P)²+1.0095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                3025
_reflns_number_total             3352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc10115h2.cif
_cod_data_source_block           syn-16b
_cod_depositor_comments
'Adding full bibliography for 7118367--7118375.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7118375
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
Br1 Br 0.290767(14) 0.80014(3) 0.517570(7) 0.01479(7) Uani 1 1 d .
C1 C 0.67272(14) 0.2126(3) 0.66868(7) 0.0118(4) Uani 1 1 d U
C2 C 0.70814(14) 0.4309(3) 0.67340(7) 0.0117(4) Uani 1 1 d U
H2 H 0.7528 0.4475 0.7097 0.014 Uiso 1 1 calc R
C3 C 0.60213(13) 0.5615(3) 0.67615(7) 0.0114(4) Uani 1 1 d U
H3 H 0.6232 0.7077 0.6763 0.014 Uiso 1 1 calc R
C4 C 0.52671(14) 0.5170(3) 0.62473(7) 0.0115(4) Uani 1 1 d U
C5 C 0.45607(14) 0.6598(3) 0.59856(7) 0.0121(4) Uani 1 1 d U
H5 H 0.4559 0.7954 0.6116 0.015 Uiso 1 1 calc R
C6 C 0.38584(13) 0.6017(3) 0.55311(7) 0.0125(4) Uani 1 1 d U
C7 C 0.38495(14) 0.4062(3) 0.53234(7) 0.0138(4) Uani 1 1 d U
H7 H 0.3359 0.3696 0.5014 0.017 Uiso 1 1 calc R
C8 C 0.45673(14) 0.2652(3) 0.55745(7) 0.0135(4) Uani 1 1 d U
H8 H 0.4588 0.1311 0.5434 0.016 Uiso 1 1 calc R
C9 C 0.52536(14) 0.3222(3) 0.60321(7) 0.0116(4) Uani 1 1 d U
C10 C 0.78449(14) 0.4872(3) 0.62529(7) 0.0114(4) Uani 1 1 d U
H10 H 0.7381 0.4874 0.5892 0.014 Uiso 1 1 calc R
C11 C 0.87727(15) 0.3303(3) 0.62094(8) 0.0178(4) Uani 1 1 d U
H11A H 0.8424 0.1998 0.6098 0.021 Uiso 1 1 calc R
H11B H 0.9142 0.3119 0.6587 0.021 Uiso 1 1 calc R
C12 C 0.96759(16) 0.3781(3) 0.57986(9) 0.0239(5) Uani 1 1 d U
H12A H 0.9306 0.4167 0.5433 0.029 Uiso 1 1 calc R
H12B H 1.0111 0.2538 0.5739 0.029 Uiso 1 1 calc R
C13 C 1.04865(16) 0.5478(3) 0.59905(9) 0.0280(5) Uani 1 1 d U
H13A H 1.0602 0.5424 0.6404 0.034 Uiso 1 1 calc R
H13B H 1.1216 0.5226 0.5831 0.034 Uiso 1 1 calc R
C14 C 1.00880(16) 0.7611(3) 0.58197(9) 0.0227(4) Uani 1 1 d U
H14A H 1.0451 0.8615 0.6077 0.027 Uiso 1 1 calc R
H14B H 1.0311 0.7908 0.5436 0.027 Uiso 1 1 calc R
C15 C 0.88450(16) 0.7795(3) 0.58370(8) 0.0178(4) Uani 1 1 d U
C16 C 0.83122(16) 0.7008(3) 0.63539(8) 0.0195(4) Uani 1 1 d U
H16A H 0.7702 0.7927 0.6451 0.023 Uiso 1 1 calc R
H16B H 0.8874 0.6984 0.6674 0.023 Uiso 1 1 calc R
C17 C 0.54386(14) 0.5115(3) 0.73008(7) 0.0139(4) Uani 1 1 d U
H17A H 0.5116 0.3741 0.7268 0.017 Uiso 1 1 calc R
H17B H 0.5999 0.5112 0.7621 0.017 Uiso 1 1 calc R
C18 C 0.45264(15) 0.6594(3) 0.74196(7) 0.0159(4) Uani 1 1 d U
C19 C 0.28760(17) 0.7030(4) 0.79112(9) 0.0303(5) Uani 1 1 d U
H19A H 0.2278 0.6983 0.7609 0.036 Uiso 1 1 calc R
H19B H 0.3120 0.8450 0.7962 0.036 Uiso 1 1 calc R
C20 C 0.24558(18) 0.6222(4) 0.84463(9) 0.0362(6) Uani 1 1 d U
H20A H 0.2271 0.4788 0.8400 0.054 Uiso 1 1 calc R
H20B H 0.1788 0.6972 0.8540 0.054 Uiso 1 1 calc R
H20C H 0.3034 0.6379 0.8749 0.054 Uiso 1 1 calc R
O1 O 0.71181(10) 0.07496(19) 0.69613(5) 0.0156(3) Uani 1 1 d U
O2 O 0.58960(10) 0.16693(17) 0.62918(5) 0.0132(3) Uani 1 1 d U
O3 O 0.82758(12) 0.8481(2) 0.54481(6) 0.0297(4) Uani 1 1 d U
O4 O 0.44555(12) 0.8288(2) 0.72461(6) 0.0286(3) Uani 1 1 d U
O5 O 0.38121(11) 0.5770(2) 0.77658(6) 0.0255(3) Uani 1 1 d U
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'
Br Br -0.2901 2.4595 '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 O2 117.14(16)
O1 C1 C2 125.82(16)
O2 C1 C2 117.04(14)
C1 C2 C3 108.04(14)
C1 C2 C10 110.46(13)
C3 C2 C10 114.85(14)
C1 C2 H2 107.7
C3 C2 H2 107.7
C10 C2 H2 107.7
C4 C3 C17 111.00(13)
C4 C3 C2 108.26(14)
C17 C3 C2 109.37(14)
C4 C3 H3 109.4
C17 C3 H3 109.4
C2 C3 H3 109.4
C9 C4 C5 118.03(15)
C9 C4 C3 118.39(15)
C5 C4 C3 123.56(16)
C6 C5 C4 119.29(16)
C6 C5 H5 120.4
C4 C5 H5 120.4
C7 C6 C5 121.99(16)
C7 C6 Br1 119.42(13)
C5 C6 Br1 118.58(13)
C8 C7 C6 118.86(16)
C8 C7 H7 120.6
C6 C7 H7 120.6
C9 C8 C7 119.16(17)
C9 C8 H8 120.4
C7 C8 H8 120.4
C8 C9 C4 122.66(16)
C8 C9 O2 115.87(15)
C4 C9 O2 121.36(15)
C11 C10 C16 111.97(14)
C11 C10 C2 110.50(14)
C16 C10 C2 109.26(14)
C11 C10 H10 108.3
C16 C10 H10 108.3
C2 C10 H10 108.3
C10 C11 C12 116.55(15)
C10 C11 H11A 108.2
C12 C11 H11A 108.2
C10 C11 H11B 108.2
C12 C11 H11B 108.2
H11A C11 H11B 107.3
C11 C12 C13 114.70(17)
C11 C12 H12A 108.6
C13 C12 H12A 108.6
C11 C12 H12B 108.6
C13 C12 H12B 108.6
H12A C12 H12B 107.6
C14 C13 C12 114.11(17)
C14 C13 H13A 108.7
C12 C13 H13A 108.7
C14 C13 H13B 108.7
C12 C13 H13B 108.7
H13A C13 H13B 107.6
C15 C14 C13 111.24(16)
C15 C14 H14A 109.4
C13 C14 H14A 109.4
C15 C14 H14B 109.4
C13 C14 H14B 109.4
H14A C14 H14B 108.0
O3 C15 C14 121.91(18)
O3 C15 C16 120.53(17)
C14 C15 C16 117.52(17)
C15 C16 C10 110.86(15)
C15 C16 H16A 109.5
C10 C16 H16A 109.5
C15 C16 H16B 109.5
C10 C16 H16B 109.5
H16A C16 H16B 108.1
C18 C17 C3 112.88(15)
C18 C17 H17A 109.0
C3 C17 H17A 109.0
C18 C17 H17B 109.0
C3 C17 H17B 109.0
H17A C17 H17B 107.8
O4 C18 O5 123.99(17)
O4 C18 C17 125.49(17)
O5 C18 C17 110.49(16)
O5 C19 C20 107.54(18)
O5 C19 H19A 110.2
C20 C19 H19A 110.2
O5 C19 H19B 110.2
C20 C19 H19B 110.2
H19A C19 H19B 108.5
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C1 O2 C9 120.20(13)
C18 O5 C19 116.36(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.9079(17)
C1 O1 1.202(2)
C1 O2 1.368(2)
C1 C2 1.509(2)
C2 C3 1.544(2)
C2 C10 1.557(2)
C2 H2 1.0000
C3 C4 1.513(2)
C3 C17 1.538(2)
C3 H3 1.0000
C4 C9 1.388(3)
C4 C5 1.394(2)
C5 C6 1.391(2)
C5 H5 0.9500
C6 C7 1.386(3)
C7 C8 1.384(3)
C7 H7 0.9500
C8 C9 1.384(2)
C8 H8 0.9500
C9 O2 1.408(2)
C10 C11 1.532(2)
C10 C16 1.536(2)
C10 H10 1.0000
C11 C12 1.538(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.539(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.538(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.502(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 O3 1.210(2)
C15 C16 1.516(3)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.509(2)
C17 H17A 0.9900
C17 H17B 0.9900
C18 O4 1.197(2)
C18 O5 1.342(2)
C19 O5 1.458(2)
C19 C20 1.500(3)
C19 H19A 0.9900
C19 H19B 0.9900
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
