#------------------------------------------------------------------------------
#$Date: 2021-11-06 21:43:59 +0100 (Sat 06 de Nov de 2021) $
#$Revision: 270514 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/82/7158282.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_7158282
loop_
_publ_author_name
'Chinnabattigalla, Sreenivasulu'
'Choudhury, Aditya'
'Gedu, Satyanarayana'
_publ_section_title
;
 [Pd]-Catalyzed para-selective allylation of phenols: access to
 4-[(E)-3-aryl/alkylprop-2-enyl]phenols.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8259
_journal_page_last               8263
_journal_paper_doi               10.1039/d1ob01489g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H22 O4'
_chemical_formula_sum            'C19 H22 O4'
_chemical_formula_weight         314.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                72.4800(10)
_cell_angle_beta                 75.8640(10)
_cell_angle_gamma                69.7340(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4709(3)
_cell_length_b                   9.9830(3)
_cell_length_c                   11.1522(4)
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.59
_cell_volume                     833.28(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19020
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.139
_diffrn_reflns_theta_min         1.939
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6965
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       irregular
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0454
_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)+(0.0548P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2539
_reflns_number_total             3672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01489g2.cif
_cod_data_source_block           mo_c19h22o4_1_0m
_cod_depositor_comments
'Adding full bibliography for 7158281--7158283.cif.'
_cod_database_code               7158282
_shelx_shelxl_version_number     2018/3
_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   0.995
_shelx_estimated_absorpt_t_min   0.992
_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 Secondary CH2 refined with riding coordinates:
 C00J(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00K(H00H,H00J,H00K), C00L(H00L,H00M,H00N), C00M(H00O,H00P,H00Q), C00N(H00R,
 H00S,H00T)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O001 O 0.00414(15) 0.68226(12) 0.13304(10) 0.0542(3) Uani 1 1 d . . . . .
O002 O 0.88136(14) 0.62258(13) 0.83869(12) 0.0576(3) Uani 1 1 d . . . . .
H002 H 0.906178 0.532608 0.856936 0.086 Uiso 1 1 calc GR . . . .
O003 O 0.25859(15) 0.78929(13) 0.11104(10) 0.0567(3) Uani 1 1 d . . . . .
O004 O -0.20935(16) 0.64015(14) 0.35178(12) 0.0641(4) Uani 1 1 d . . . . .
C005 C 0.1635(2) 0.76797(16) 0.22933(14) 0.0432(4) Uani 1 1 d . . . . .
C006 C 0.1928(2) 0.79423(16) 0.33562(14) 0.0432(4) Uani 1 1 d . . . . .
H006 H 0.283142 0.829876 0.329479 0.052 Uiso 1 1 calc R . . . .
C007 C 0.08735(19) 0.76740(16) 0.45201(14) 0.0431(4) Uani 1 1 d . . . . .
C008 C 0.0283(2) 0.71411(16) 0.23839(14) 0.0442(4) Uani 1 1 d . . . . .
C009 C 0.4452(2) 0.66303(16) 0.80189(14) 0.0435(4) Uani 1 1 d . . . . .
C00A C 0.2069(2) 0.86485(17) 0.58134(15) 0.0489(4) Uani 1 1 d . . . . .
H00A H 0.272943 0.904162 0.508533 0.059 Uiso 1 1 calc R . . . .
C00B C 0.6674(2) 0.83003(17) 0.75350(15) 0.0501(4) Uani 1 1 d . . . . .
H00B H 0.740943 0.886492 0.737049 0.060 Uiso 1 1 calc R . . . .
C00C C 0.3916(2) 0.81407(16) 0.74513(13) 0.0440(4) Uani 1 1 d . . . . .
C00D C 0.7198(2) 0.68152(16) 0.80896(14) 0.0436(4) Uani 1 1 d . . . . .
C00E C 0.6086(2) 0.59966(16) 0.83289(14) 0.0438(4) Uani 1 1 d . . . . .
H00E H 0.643896 0.499670 0.870674 0.053 Uiso 1 1 calc R . . . .
C00F C 0.1111(2) 0.79313(18) 0.56853(15) 0.0491(4) Uani 1 1 d . . . . .
H00F H 0.049533 0.752801 0.643626 0.059 Uiso 1 1 calc R . . . .
C00G C 0.5055(2) 0.89424(17) 0.72263(15) 0.0502(4) Uani 1 1 d . . . . .
H00G H 0.471358 0.994485 0.685529 0.060 Uiso 1 1 calc R . . . .
C00H C -0.0776(2) 0.68836(16) 0.35389(15) 0.0458(4) Uani 1 1 d . . . . .
C00I C -0.0465(2) 0.71289(17) 0.46021(14) 0.0470(4) Uani 1 1 d . . . . .
H00I H -0.115596 0.692768 0.538037 0.056 Uiso 1 1 calc R . . . .
C00J C 0.2171(2) 0.88792(18) 0.70633(16) 0.0536(4) Uani 1 1 d . . . . .
H00C H 0.134242 0.849803 0.772133 0.064 Uiso 1 1 calc R . . . .
H00D H 0.187192 0.992553 0.699880 0.064 Uiso 1 1 calc R . . . .
C00K C 0.3291(2) 0.56888(19) 0.83088(18) 0.0643(5) Uani 1 1 d . . . . .
H00H H 0.221925 0.614037 0.877128 0.096 Uiso 1 1 calc GR . . . .
H00J H 0.380317 0.473514 0.881324 0.096 Uiso 1 1 calc GR . . . .
H00K H 0.310985 0.558948 0.752709 0.096 Uiso 1 1 calc GR . . . .
C00L C 0.3988(2) 0.8428(2) 0.09440(18) 0.0651(5) Uani 1 1 d . . . . .
H00L H 0.458323 0.846892 0.008884 0.098 Uiso 1 1 calc GR . . . .
H00M H 0.474500 0.778362 0.153220 0.098 Uiso 1 1 calc GR . . . .
H00N H 0.358528 0.939575 0.109795 0.098 Uiso 1 1 calc GR . . . .
C00M C -0.1066(3) 0.8020(2) 0.05696(19) 0.0766(6) Uani 1 1 d . . . . .
H00O H -0.122869 0.770687 -0.011374 0.115 Uiso 1 1 calc GR . . . .
H00P H -0.056986 0.881401 0.022509 0.115 Uiso 1 1 calc GR . . . .
H00Q H -0.214547 0.834473 0.108466 0.115 Uiso 1 1 calc GR . . . .
C00N C -0.3274(2) 0.6202(2) 0.4657(2) 0.0709(5) Uani 1 1 d . . . . .
H00R H -0.415827 0.590499 0.450697 0.106 Uiso 1 1 calc GR . . . .
H00S H -0.376675 0.710950 0.492255 0.106 Uiso 1 1 calc GR . . . .
H00T H -0.269583 0.545687 0.531169 0.106 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 0.0033 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
C008 O001 C00M 113.89(12) . . ?
C005 O003 C00L 118.04(12) . . ?
C00H O004 C00N 117.69(13) . . ?
O003 C005 C006 125.31(14) . . ?
O003 C005 C008 114.67(13) . . ?
C006 C005 C008 120.01(14) . . ?
C005 C006 C007 120.18(14) . . ?
C006 C007 C00F 122.98(14) . . ?
C00I C007 C006 119.36(13) . . ?
C00I C007 C00F 117.66(13) . . ?
O001 C008 C005 119.66(13) . . ?
O001 C008 C00H 120.39(14) . . ?
C00H C008 C005 119.92(13) . . ?
C00C C009 C00K 121.38(14) . . ?
C00E C009 C00C 119.28(14) . . ?
C00E C009 C00K 119.34(14) . . ?
C00F C00A C00J 124.27(16) . . ?
C00G C00B C00D 119.65(15) . . ?
C009 C00C C00J 121.52(14) . . ?
C00G C00C C009 118.05(14) . . ?
C00G C00C C00J 120.42(14) . . ?
O002 C00D C00B 117.64(14) . . ?
O002 C00D C00E 123.05(14) . . ?
C00B C00D C00E 119.31(15) . . ?
C00D C00E C009 121.59(14) . . ?
C00A C00F C007 129.03(15) . . ?
C00B C00G C00C 122.13(14) . . ?
O004 C00H C008 115.37(13) . . ?
O004 C00H C00I 124.78(14) . . ?
C00I C00H C008 119.85(14) . . ?
C00H C00I C007 120.66(14) . . ?
C00A C00J C00C 113.03(13) . . ?
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
O001 C008 1.3823(17) . ?
O001 C00M 1.425(2) . ?
O002 C00D 1.3697(19) . ?
O003 C005 1.3656(18) . ?
O003 C00L 1.415(2) . ?
O004 C00H 1.3669(19) . ?
O004 C00N 1.421(2) . ?
C005 C006 1.383(2) . ?
C005 C008 1.396(2) . ?
C006 C007 1.395(2) . ?
C007 C00F 1.470(2) . ?
C007 C00I 1.391(2) . ?
C008 C00H 1.388(2) . ?
C009 C00C 1.404(2) . ?
C009 C00E 1.389(2) . ?
C009 C00K 1.502(2) . ?
C00A C00F 1.308(2) . ?
C00A C00J 1.506(2) . ?
C00B C00D 1.380(2) . ?
C00B C00G 1.378(2) . ?
C00C C00G 1.389(2) . ?
C00C C00J 1.510(2) . ?
C00D C00E 1.380(2) . ?
C00H C00I 1.381(2) . ?
