#------------------------------------------------------------------------------
#$Date: 2019-11-08 02:23:24 +0100 (Fri 08 de Nov de 2019) $
#$Revision: 225045 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/66/7156682.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_7156682
loop_
_publ_author_name
'Khanvilkar, Aditya N.'
'Samanta, Sudeep G.'
'Bedekar, Ashutosh V.'
_publ_section_title
;
 Applications of chiral naphthyloxycyclohexanols in deracemization of
 α-substituted carboxylic acids by dynamic thermodynamic resolution.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2670
_journal_page_last               2683
_journal_paper_doi               10.1039/c8ob02896f
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H26 O5'
_chemical_formula_sum            'C26 H26 O5'
_chemical_formula_weight         418.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_update_record
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2235(6)
_cell_length_b                   15.8364(13)
_cell_length_c                   17.2177(13)
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9400
_cell_measurement_theta_min      4.2630
_cell_volume                     2242.3(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.8669
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13939
_diffrn_reflns_theta_full        28.9593
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.2396
_exptl_crystal_F_000             888.4921
_refine_diff_density_max         0.2894
_refine_diff_density_min         -0.3311
_refine_diff_density_rms         0.0821
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_d_res_high            0.7339
_refine_ls_d_res_low             5.8279
_refine_ls_goodness_of_fit_ref   1.0707
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0707
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0637P)²+0.0510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.821
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                3857
_reflns_number_total             5147
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02896f2.cif
_cod_data_source_block           exp_1012
_cod_depositor_comments
'Adding full bibliography for 7156681--7156686.cif.'
_cod_database_code               7156682
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H29 of C29, H8 of C8, H30 of C30, H7 of C7, H6 of C6, {H15a,H15b} of C15,
  {H16a,H16b} of C16, H9 of C9, H27 of C27, H31 of C31, H2 of C2, H3 of C3, H28
  of C28, H4 of C4, H12 of C12, H13 of C13, H20 of C20, {H17a,H17b} of C17,
  {H14a,H14b} of C14
 At 1.5 times of:
  {H24a,H24b,H24c} of C24
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C27(H27), C31(H31), C2(H2), C3(H3), C28(H28), C4(H4), C29(H29),
 C8(H8), C30(H30), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,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_refinement_flags_posn
O11 O 0.26314(16) 0.08356(8) 0.04388(8) 0.0404(3) Uani 1.000000 .
O18 O 0.40510(15) 0.13027(9) 0.18552(7) 0.0370(3) Uani 1.000000 .
O21 O 0.75296(17) 0.00250(10) 0.22763(9) 0.0506(4) Uani 1.000000 .
C12 C 0.2016(2) 0.15514(12) 0.08615(10) 0.0326(4) Uani 1.000000 .
H12 H 0.1167(2) 0.13621(12) 0.12211(10) 0.0391(5) Uiso 1.000000 R
C13 C 0.3410(2) 0.19243(12) 0.13204(10) 0.0323(4) Uani 1.000000 .
H13 H 0.4270(2) 0.21107(12) 0.09655(10) 0.0388(5) Uiso 1.000000 R
C20 C 0.5905(2) 0.03468(14) 0.23640(11) 0.0398(5) Uani 1.000000 .
H20 H 0.5839(2) 0.06630(14) 0.28523(11) 0.0478(6) Uiso 1.000000 R
C1 C 0.1567(2) 0.02173(13) 0.02183(11) 0.0392(5) Uani 1.000000 .
O25 O 0.62798(18) 0.10511(12) 0.11294(9) 0.0639(5) Uani 1.000000 .
C17 C 0.1317(3) 0.22120(13) 0.03220(11) 0.0416(5) Uani 1.000000 .
H17a H 0.2147(3) 0.23931(13) -0.00420(11) 0.0499(6) Uiso 1.000000 R
H17b H 0.0427(3) 0.19695(13) 0.00274(11) 0.0499(6) Uiso 1.000000 R
C19 C 0.5479(2) 0.09384(13) 0.16942(11) 0.0381(5) Uani 1.000000 .
C26 C 0.4793(2) -0.03998(13) 0.24126(11) 0.0387(5) Uani 1.000000 .
C10 C 0.2314(3) -0.04829(13) -0.01605(11) 0.0441(5) Uani 1.000000 .
C14 C 0.2810(3) 0.26642(13) 0.17940(12) 0.0453(5) Uani 1.000000 .
H14a H 0.2002(3) 0.24707(13) 0.21641(12) 0.0544(6) Uiso 1.000000 R
H14b H 0.3709(3) 0.29058(13) 0.20828(12) 0.0544(6) Uiso 1.000000 R
C15 C 0.2065(3) 0.33368(14) 0.12722(13) 0.0524(6) Uani 1.000000 .
H15a H 0.1636(3) 0.37914(14) 0.15895(13) 0.0628(7) Uiso 1.000000 R
H15b H 0.2900(3) 0.35700(14) 0.09368(13) 0.0628(7) Uiso 1.000000 R
C16 C 0.0708(3) 0.29680(14) 0.07789(13) 0.0506(6) Uani 1.000000 .
H16a H 0.0307(3) 0.33949(14) 0.04231(13) 0.0608(7) Uiso 1.000000 R
H16b H -0.0186(3) 0.27963(14) 0.11111(13) 0.0608(7) Uiso 1.000000 R
C9 C 0.4005(3) -0.05150(15) -0.02979(12) 0.0520(6) Uani 1.000000 .
H9 H 0.4664(3) -0.00678(15) -0.01445(12) 0.0624(7) Uiso 1.000000 R
C27 C 0.4155(3) -0.06229(16) 0.31250(13) 0.0519(6) Uani 1.000000 .
H27 H 0.4398(3) -0.02998(16) 0.35608(13) 0.0623(7) Uiso 1.000000 R
C31 C 0.4419(3) -0.08714(17) 0.17673(14) 0.0597(6) Uani 1.000000 .
H31 H 0.4832(3) -0.07207(17) 0.12839(14) 0.0716(8) Uiso 1.000000 R
C2 C -0.0081(3) 0.02364(16) 0.03373(14) 0.0535(6) Uani 1.000000 .
H2 H -0.0562(3) 0.06990(16) 0.05779(14) 0.0642(7) Uiso 1.000000 R
C5 C 0.1322(3) -0.11614(16) -0.04002(15) 0.0610(7) Uani 1.000000 .
C22 C 0.8759(3) 0.0562(2) 0.24410(18) 0.0676(8) Uani 1.000000 .
C3 C -0.1038(3) -0.04508(19) 0.00919(18) 0.0744(8) Uani 1.000000 .
H3 H -0.2155(3) -0.04398(19) 0.01758(18) 0.0893(10) Uiso 1.000000 R
C28 C 0.3176(3) -0.1310(2) 0.3196(2) 0.0737(8) Uani 1.000000 .
H28 H 0.2750(3) -0.1454(2) 0.3679(2) 0.0884(10) Uiso 1.000000 R
O23 O 0.8538(3) 0.12819(15) 0.25922(18) 0.1126(10) Uani 1.000000 .
C4 C -0.0364(4) -0.11241(19) -0.02623(18) 0.0812(9) Uani 1.000000 .
H4 H -0.1023(4) -0.15707(19) -0.04179(18) 0.0974(11) Uiso 1.000000 R
C29 C 0.2818(3) -0.17875(19) 0.2563(2) 0.0837(10) Uani 1.000000 .
H29 H 0.2160(3) -0.22617(19) 0.2617(2) 0.1004(12) Uiso 1.000000 R
C8 C 0.4675(4) -0.12007(19) -0.06554(16) 0.0737(8) Uani 1.000000 .
H8 H 0.5792(4) -0.12185(19) -0.07408(16) 0.0884(10) Uiso 1.000000 R
C30 C 0.3421(4) -0.1575(2) 0.1841(2) 0.0812(9) Uani 1.000000 .
H30 H 0.3163(4) -0.1900(2) 0.1408(2) 0.0975(11) Uiso 1.000000 R
C24 C 1.0349(3) 0.0114(2) 0.2430(2) 0.0900(12) Uani 1.000000 .
H24a H 1.0454(13) -0.0196(13) 0.1954(7) 0.1350(17) Uiso 1.000000 GR
H24b H 1.1215(3) 0.0518(3) 0.2469(14) 0.1350(17) Uiso 1.000000 GR
H24c H 1.0403(13) -0.0270(12) 0.2861(9) 0.1350(17) Uiso 1.000000 GR
C7 C 0.3709(5) -0.1874(2) -0.0894(2) 0.0900(10) Uani 1.000000 .
H7 H 0.4179(5) -0.2337(2) -0.1139(2) 0.1080(12) Uiso 1.000000 R
C6 C 0.2083(5) -0.18559(19) -0.07695(19) 0.0868(10) Uani 1.000000 .
H6 H 0.1452(5) -0.23106(19) -0.09304(19) 0.1042(12) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O11 C12 118.65(15)
C19 O18 C13 118.77(14)
C22 O21 C20 116.74(19)
C13 C12 O11 107.77(15)
C17 C12 O11 111.59(15)
C17 C12 C13 109.80(16)
C12 C13 O18 110.05(15)
C14 C13 O18 107.65(14)
C14 C13 C12 109.71(16)
C19 C20 O21 110.57(16)
C26 C20 O21 107.08(17)
C26 C20 C19 112.75(16)
C10 C1 O11 114.10(17)
C2 C1 O11 125.1(2)
C2 C1 C10 120.8(2)
C16 C17 C12 110.66(15)
C20 C19 O18 108.04(15)
O25 C19 O18 126.28(18)
O25 C19 C20 125.68(18)
C27 C26 C20 118.95(19)
C31 C26 C20 121.39(19)
C31 C26 C27 119.6(2)
C9 C10 C1 122.0(2)
C5 C10 C1 118.5(2)
C5 C10 C9 119.6(2)
C15 C14 C13 110.84(16)
C16 C15 C14 110.89(19)
C15 C16 C17 110.51(19)
C8 C9 C10 120.2(2)
C28 C27 C26 120.7(3)
C30 C31 C26 119.6(3)
C3 C2 C1 119.4(2)
C4 C5 C10 119.2(2)
C6 C5 C10 117.8(3)
C6 C5 C4 122.9(3)
O23 C22 O21 122.5(2)
C24 C22 O21 110.7(3)
C24 C22 O23 126.7(3)
C4 C3 C2 121.2(3)
C29 C28 C27 120.1(3)
C3 C4 C5 121.0(3)
C30 C29 C28 120.6(3)
C7 C8 C9 120.8(3)
C29 C30 C31 119.3(3)
C6 C7 C8 120.1(3)
C7 C6 C5 121.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O11 C12 1.439(2)
O11 C1 1.367(2)
O18 C13 1.447(2)
O18 C19 1.337(2)
O21 C20 1.438(2)
O21 C22 1.352(3)
C12 C13 1.512(3)
C12 C17 1.512(3)
C13 C14 1.511(3)
C20 C19 1.527(3)
C20 C26 1.497(3)
C1 C10 1.426(3)
C1 C2 1.370(3)
O25 C19 1.188(2)
C17 C16 1.518(3)
C26 C27 1.380(3)
C26 C31 1.373(3)
C10 C9 1.412(3)
C10 C5 1.411(3)
C14 C15 1.522(3)
C15 C16 1.519(3)
C9 C8 1.365(3)
C27 C28 1.359(4)
C31 C30 1.390(4)
C2 C3 1.408(3)
C5 C4 1.408(4)
C5 C6 1.416(4)
C22 O23 1.183(4)
C22 C24 1.488(4)
C3 C4 1.348(4)
C28 C29 1.359(4)
C29 C30 1.381(5)
C8 C7 1.392(5)
C7 C6 1.354(5)
