#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:17:51 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/69/7126944.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_7126944
loop_
_publ_author_name
'Zhang, Yu-Long'
'Zhao, Zhen-Ni'
'Li, Wang-Lai'
'Li, Jing-Jie'
'Kalita, Subarna Jyoti'
'Schneider, Uwe'
'Huang, Yi-Yong'
_publ_section_title
;
 Catalytic asymmetric aldehyde prenylation and application in the total
 synthesis of (-)-rosiridol and (-)-bifurcadiol.
;
_journal_issue                   69
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10030
_journal_page_last               10033
_journal_paper_doi               10.1039/d0cc00367k
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H15 Br O3'
_chemical_formula_sum            'C13 H15 Br O3'
_chemical_formula_weight         299.16
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-24
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2019-12-02 deposited with the CCDC.	2020-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.046(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8308(5)
_cell_length_b                   4.8800(2)
_cell_length_c                   12.3237(6)
_cell_measurement_reflns_used    3360
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.93
_cell_measurement_theta_min      3.84
_cell_volume                     664.04(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4261
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        63.911
_diffrn_reflns_theta_max         63.911
_diffrn_reflns_theta_min         3.843
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.184
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.1807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.150
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details
; 
 Flack x determined using 630 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.19(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1931
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1272P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.764
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                1817
_reflns_number_total             1931
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00367k2.cif
_cod_data_source_block           cu_190531b_0m
_cod_depositor_comments          'Adding full bibliography for 7126944.cif.'
_cod_database_code               7126944
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_max   0.680
_shelx_estimated_absorpt_t_min   0.634
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C8(H8) 
2.b Secondary CH2 refined with riding coordinates: 
 C1(H1A,H1B), C9(H9A,H9B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C4(H4), C7(H7), C10(H10) 
2.d Idealised Me refined as rotating group: 
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3) 
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.88522(7) -0.0940(4) 0.93772(8) 0.0446(4) Uani 1 1 d . . . . .
C1 C 0.6205(12) 0.745(4) 0.5401(12) 0.066(3) Uani 1 1 d . . . . .
H1A H 0.5662 0.7006 0.4620 0.079 Uiso 1 1 calc R . . . .
H1B H 0.6508 0.9291 0.5398 0.079 Uiso 1 1 calc R . . . .
C2 C 0.7188(10) 0.444(3) 0.6795(9) 0.046(3) Uani 1 1 d . . . . .
C3 C 0.6218(10) 0.548(2) 0.7037(10) 0.044(2) Uani 1 1 d . . . . .
C4 C 0.5999(10) 0.460(2) 0.8019(9) 0.043(3) Uani 1 1 d . . . . .
H4 H 0.5342 0.5250 0.8187 0.052 Uiso 1 1 calc R . . . .
C5 C 0.6805(8) 0.270(2) 0.8742(9) 0.035(2) Uani 1 1 d . . . . .
C6 C 0.7747(9) 0.171(2) 0.8460(9) 0.041(2) Uani 1 1 d . . . . .
C7 C 0.7957(10) 0.254(3) 0.7448(9) 0.046(3) Uani 1 1 d . . . . .
H7 H 0.8584 0.1825 0.7248 0.055 Uiso 1 1 calc R . . . .
C8 C 0.6645(9) 0.189(2) 0.9881(9) 0.037(2) Uani 1 1 d . . . . .
H8 H 0.6862 -0.0045 1.0041 0.045 Uiso 1 1 calc R . . . .
C9 C 0.7455(10) 0.360(3) 1.0897(10) 0.053(3) Uani 1 1 d . . . . .
H9A H 0.8284 0.3453 1.0930 0.064 Uiso 1 1 calc R . . . .
H9B H 0.7216 0.5506 1.0758 0.064 Uiso 1 1 calc R . . . .
C10 C 0.7405(14) 0.275(4) 1.2054(13) 0.073(4) Uani 1 1 d . . . . .
H10 H 0.6708 0.3261 1.2186 0.087 Uiso 1 1 calc R . . . .
C11 C 0.8190(14) 0.142(3) 1.2882(12) 0.069(4) Uani 1 1 d . . . . .
C12 C 0.936(2) 0.042(6) 1.2839(18) 0.135(12) Uani 1 1 d . . . . .
H12A H 0.9485 -0.1446 1.3096 0.203 Uiso 1 1 calc GR . . . .
H12B H 1.0008 0.1536 1.3336 0.203 Uiso 1 1 calc GR . . . .
H12C H 0.9342 0.0538 1.2055 0.203 Uiso 1 1 calc GR . . . .
C13 C 0.801(2) 0.064(6) 1.4003(16) 0.131(10) Uani 1 1 d . . . . .
H13A H 0.7359 0.1708 1.4081 0.197 Uiso 1 1 calc GR . . . .
H13B H 0.8738 0.0980 1.4653 0.197 Uiso 1 1 calc GR . . . .
H13C H 0.7805 -0.1274 1.3982 0.197 Uiso 1 1 calc GR . . . .
O1 O 0.7171(10) 0.558(2) 0.5759(8) 0.080(3) Uani 1 1 d . . . . .
O2 O 0.5567(9) 0.727(2) 0.6204(8) 0.063(2) Uani 1 1 d . . . . .
O3 O 0.5411(7) 0.2247(15) 0.9780(8) 0.0514(19) Uani 1 1 d . . . . .
H3 H 0.5320 0.3791 0.9998 0.077 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1A C1 H1B 108.4 . . ?
O1 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
O1 C1 O2 108.2(10) . . ?
O2 C1 H1A 110.1 . . ?
O2 C1 H1B 110.1 . . ?
C3 C2 O1 108.4(11) . . ?
C7 C2 C3 123.9(10) . . ?
C7 C2 O1 127.6(10) . . ?
C2 C3 C4 120.3(11) . . ?
O2 C3 C2 111.2(10) . . ?
O2 C3 C4 128.6(10) . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.4(10) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C8 118.2(8) . . ?
C6 C5 C4 120.2(10) . . ?
C6 C5 C8 121.4(10) . . ?
C5 C6 Br1 122.6(8) . . ?
C5 C6 C7 122.6(11) . . ?
C7 C6 Br1 114.8(8) . . ?
C2 C7 C6 115.5(10) . . ?
C2 C7 H7 122.2 . . ?
C6 C7 H7 122.2 . . ?
C5 C8 H8 108.7 . . ?
C9 C8 C5 111.3(8) . . ?
C9 C8 H8 108.7 . . ?
O3 C8 C5 110.2(8) . . ?
O3 C8 H8 108.7 . . ?
O3 C8 C9 109.1(8) . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.6(11) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C9 C10 H10 115.5 . . ?
C11 C10 C9 129.0(13) . . ?
C11 C10 H10 115.5 . . ?
C10 C11 C12 123.6(13) . . ?
C10 C11 C13 123.4(15) . . ?
C12 C11 C13 112.9(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 O1 C1 106.8(9) . . ?
C3 O2 C1 105.3(9) . . ?
C8 O3 H3 109.5 . . ?
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
Br1 C6 1.896(11) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 O1 1.403(18) . ?
C1 O2 1.446(15) . ?
C2 C3 1.380(16) . ?
C2 C7 1.345(19) . ?
C2 O1 1.386(14) . ?
C3 C4 1.394(14) . ?
C3 O2 1.358(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(16) . ?
C5 C6 1.369(14) . ?
C5 C8 1.534(14) . ?
C6 C7 1.416(16) . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.522(16) . ?
C8 O3 1.431(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.506(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.28(2) . ?
C11 C12 1.49(2) . ?
C11 C13 1.522(17) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O3 H3 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O3 0.82 1.96 2.752(6) 162.5 2_657
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C6 C7 C2 -179.3(9) . . . . ?
C2 C3 C4 C5 1.1(17) . . . . ?
C2 C3 O2 C1 -2.2(15) . . . . ?
C3 C2 C7 C6 -3(2) . . . . ?
C3 C2 O1 C1 3.1(16) . . . . ?
C3 C4 C5 C6 -1.8(16) . . . . ?
C3 C4 C5 C8 174.8(10) . . . . ?
C4 C3 O2 C1 179.5(13) . . . . ?
C4 C5 C6 Br1 -178.4(8) . . . . ?
C4 C5 C6 C7 0.2(16) . . . . ?
C4 C5 C8 C9 -95.1(11) . . . . ?
C4 C5 C8 O3 26.1(13) . . . . ?
C5 C6 C7 C2 2.0(17) . . . . ?
C5 C8 C9 C10 -175.6(10) . . . . ?
C6 C5 C8 C9 81.5(12) . . . . ?
C6 C5 C8 O3 -157.3(9) . . . . ?
C7 C2 C3 C4 1(2) . . . . ?
C7 C2 C3 O2 -177.1(13) . . . . ?
C7 C2 O1 C1 179.5(15) . . . . ?
C8 C5 C6 Br1 5.2(14) . . . . ?
C8 C5 C6 C7 -176.2(10) . . . . ?
C8 C9 C10 C11 105(2) . . . . ?
C9 C10 C11 C12 0(3) . . . . ?
C9 C10 C11 C13 -178.5(19) . . . . ?
O1 C1 O2 C3 4.1(16) . . . . ?
O1 C2 C3 C4 177.9(11) . . . . ?
O1 C2 C3 O2 -0.5(16) . . . . ?
O1 C2 C7 C6 -178.7(12) . . . . ?
O2 C1 O1 C2 -4.4(16) . . . . ?
O2 C3 C4 C5 179.2(11) . . . . ?
O3 C8 C9 C10 62.5(13) . . . . ?
