#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:23:24 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225045 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/66/7156681.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_7156681
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 rm
_chemical_formula_moiety         'C19 H21 Br O3'
_chemical_formula_sum            'C19 H21 Br O3'
_chemical_formula_weight         377.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_update_record
;
2018-07-07 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.420(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6654(18)
_cell_length_b                   5.3717(12)
_cell_length_c                   17.065(3)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9870
_cell_measurement_theta_min      3.4620
_cell_volume                     882.0(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.6863
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4672
_diffrn_reflns_theta_full        28.9436
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    2.342
_exptl_crystal_density_diffrn    1.4205
_exptl_crystal_F_000             388.0
_refine_diff_density_max         0.7902
_refine_diff_density_min         -0.6905
_refine_diff_density_rms         0.1387
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_d_res_high            0.7343
_refine_ls_d_res_low             5.6628
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0588
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.0549
_refine_ls_shift/su_mean         0.0017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0967P)²+0.4416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2044
_reflns_Friedel_coverage         0.466
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              6
_reflns_limit_k_min              -7
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                1931
_reflns_number_total             4672
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ob02896f2.cif
_cod_data_source_block           exp_1059
_cod_depositor_comments
'Adding full bibliography for 7156681--7156686.cif.'
_cod_database_code               7156681
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H6 of C6, {H15a,H15b} of C15, {H14a,H14b} of C14, H13 of C13,
  H7 of C7, H10 of C10, H5 of C5, H4 of C4, {H17a,H17b} of C17, H20 of C20,
  {H16a,H16b} of C16, H9 of C9, H2 of C2
 At 1.5 times of:
  {H18a,H18b,H18c} of C18
2.a Ternary CH refined with riding coordinates:
 C20(H20), C13(H13), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C16(H16a,H16b), C14(H14a,H14b), C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,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_refinement_flags_posn
Br21 Br -1.07504(9) -0.73832(10) -0.22791(5) 0.1061(6) Uani 1.000000 .
O18 O -0.8167(4) -0.4134(9) -0.1529(3) 0.0506(12) Uani 1.000000 .
O11 O -0.6696(5) -0.6782(8) -0.2534(3) 0.0541(13) Uani 1.000000 .
O23 O -0.8304(5) -0.6929(12) -0.0568(3) 0.079(2) Uani 1.000000 .
C19 C -0.8841(7) -0.5656(14) -0.1094(4) 0.0460(17) Uani 1.000000 .
C20 C -1.0378(7) -0.5517(14) -0.1316(5) 0.057(2) Uani 1.000000 .
C17 C -0.4583(8) -0.4380(14) -0.2165(5) 0.0525(19) Uani 1.000000 .
C13 C -0.6643(7) -0.4164(13) -0.1430(4) 0.0428(16) Uani 1.000000 .
C12 C -0.6144(7) -0.4465(13) -0.2236(4) 0.0423(16) Uani 1.000000 .
C16 C -0.4064(7) -0.1973(16) -0.1791(4) 0.061(2) Uani 1.000000 .
C1 C -0.7035(7) -0.7043(13) -0.3332(4) 0.0458(16) Uani 1.000000 .
C8 C -0.7879(8) -0.8021(14) -0.4916(4) 0.057(2) Uani 1.000000 .
C9 C -0.8337(9) -0.9458(15) -0.4311(5) 0.062(2) Uani 1.000000 .
C3 C -0.6951(8) -0.5985(14) -0.4697(5) 0.0537(19) Uani 1.000000 .
C2 C -0.6580(8) -0.5556(15) -0.3886(4) 0.0555(19) Uani 1.000000 .
C7 C -0.8257(11) -0.8396(17) -0.5720(5) 0.080(3) Uani 1.000000 .
C6 C -0.7790(11) -0.694(2) -0.6270(5) 0.087(3) Uani 1.000000 .
C14 C -0.6153(7) -0.1739(13) -0.1048(4) 0.0480(17) Uani 1.000000 .
C15 C -0.4564(8) -0.1639(15) -0.0978(4) 0.060(2) Uani 1.000000 .
C4 C -0.6482(10) -0.4500(17) -0.5301(5) 0.073(2) Uani 1.000000 .
C5 C -0.6879(13) -0.501(2) -0.6059(5) 0.093(3) Uani 1.000000 .
C10 C -0.7911(8) -0.9031(14) -0.3536(5) 0.058(2) Uani 1.000000 .
C18 C -1.1274(5) -0.6939(17) -0.0713(3) 0.053(2) Uani 1.000000 .
H10 H -0.8206(8) -1.0067(14) -0.3148(5) 0.069(2) Uiso 1.000000 R
H9 H -0.8955(9) -1.0754(15) -0.4440(5) 0.074(3) Uiso 1.000000 R
H2 H -0.6008(8) -0.4216(15) -0.3733(4) 0.067(2) Uiso 1.000000 R
H4 H -0.5892(10) -0.3163(17) -0.5173(5) 0.087(3) Uiso 1.000000 R
H5 H -0.6537(13) -0.404(2) -0.6450(5) 0.112(4) Uiso 1.000000 R
H6 H -0.8076(11) -0.723(2) -0.6798(5) 0.104(4) Uiso 1.000000 R
H7 H -0.8854(11) -0.9701(17) -0.5875(5) 0.096(4) Uiso 1.000000 R
H20 H -1.0684(7) -0.3785(14) -0.1388(5) 0.068(2) Uiso 1.000000 R
H17a H -0.4215(8) -0.5770(14) -0.1847(5) 0.063(2) Uiso 1.000000 R
H17b H -0.4256(8) -0.4533(14) -0.2683(5) 0.063(2) Uiso 1.000000 R
H13 H -0.6318(7) -0.5565(13) -0.1094(4) 0.0514(19) Uiso 1.000000 R
H12 H -0.6515(7) -0.3108(13) -0.2578(4) 0.0508(19) Uiso 1.000000 R
H16a H -0.3057(7) -0.1958(16) -0.1747(4) 0.073(2) Uiso 1.000000 R
H16b H -0.4392(7) -0.0591(16) -0.2125(4) 0.073(2) Uiso 1.000000 R
H14a H -0.6531(7) -0.0350(13) -0.1362(4) 0.058(2) Uiso 1.000000 R
H14b H -0.6480(7) -0.1612(13) -0.0529(4) 0.058(2) Uiso 1.000000 R
H15a H -0.4185(8) -0.2948(15) -0.0630(4) 0.071(3) Uiso 1.000000 R
H15b H -0.4246(8) -0.0051(15) -0.0759(4) 0.071(3) Uiso 1.000000 R
H18a H -1.2244(6) -0.662(8) -0.0849(19) 0.080(3) Uiso 1.000000 GR
H18b H -1.110(4) -0.8696(19) -0.074(2) 0.080(3) Uiso 1.000000 GR
H18c H -1.101(4) -0.636(7) -0.0188(5) 0.080(3) Uiso 1.000000 GR
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'
Br -0.28346 2.55990 '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
C13 O18 C19 118.2(5)
C1 O11 C12 119.1(5)
O23 C19 O18 124.7(6)
C20 C19 O18 111.0(6)
C20 C19 O23 124.2(7)
C19 C20 Br21 106.8(5)
C18 C20 Br21 103.4(5)
C18 C20 C19 113.4(6)
C16 C17 C12 110.6(6)
C12 C13 O18 107.4(5)
C14 C13 O18 108.1(6)
C14 C13 C12 111.8(6)
C17 C12 O11 113.2(6)
C13 C12 O11 106.1(5)
C13 C12 C17 109.1(6)
C15 C16 C17 111.4(6)
C2 C1 O11 124.9(7)
C10 C1 O11 114.2(7)
C10 C1 C2 120.9(7)
C3 C8 C9 117.5(7)
C7 C8 C9 125.0(8)
C7 C8 C3 117.5(8)
C10 C9 C8 122.4(8)
C2 C3 C8 118.1(7)
C4 C3 C8 118.3(7)
C4 C3 C2 123.5(8)
C3 C2 C1 121.5(8)
C6 C7 C8 122.1(9)
C5 C6 C7 120.4(8)
C15 C14 C13 109.5(6)
C14 C15 C16 109.1(6)
C5 C4 C3 120.5(9)
C4 C5 C6 121.2(10)
C9 C10 C1 119.6(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br21 C20 1.929(8)
O18 C19 1.318(8)
O18 C13 1.466(8)
O11 C12 1.428(8)
O11 C1 1.376(8)
O23 C19 1.206(9)
C19 C20 1.500(10)
C20 C18 1.600(9)
C17 C12 1.503(9)
C17 C16 1.507(11)
C13 C12 1.509(9)
C13 C14 1.512(10)
C16 C15 1.521(10)
C1 C2 1.344(10)
C1 C10 1.387(11)
C8 C9 1.394(11)
C8 C3 1.441(11)
C8 C7 1.401(11)
C9 C10 1.367(12)
C3 C2 1.415(11)
C3 C4 1.412(12)
C7 C6 1.333(13)
C6 C5 1.388(15)
C14 C15 1.531(10)
C4 C5 1.342(13)
