#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:27:21 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/98/7059813.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_7059813
loop_
_publ_author_name
'Jiménez-Cruz, Juan C.'
'Guzmán-Mejía, Ramón'
'Juaristi, Eusebio'
'Sánchez-Antonio, Omar'
'García-Revilla, Marco A.'
'González-Campos, J. Betzabe'
'Aviña-Verduzco, Judit'
_publ_section_title
;
 Preparation of aromatic γ-hydroxyketones by means of Heck coupling of
 aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(ii) glycine
 complex under microwave irradiation
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13382
_journal_page_last               13392
_journal_paper_doi               10.1039/D0NJ02630A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_name_systematic        4-hydroxy-1,4-bis(4-methoxyphenyl)butan-1-one
_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     dual
_audit_creation_date             2018-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-23 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.648(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1124(5)
_cell_length_b                   5.2113(2)
_cell_length_c                   13.3792(6)
_cell_measurement_reflns_used    9358
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      62.29
_cell_measurement_theta_min      3.31
_cell_volume                     773.22(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      273.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18860
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        62.540
_diffrn_reflns_theta_max         62.540
_diffrn_reflns_theta_min         3.310
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.5665
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1304 before and 0.0977 after correction. The Ratio of minimum to maximum transmission is 0.7531. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       ROMBO
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 817 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0511
_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)+(0.0713P)²+0.1608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2127
_reflns_number_total             2456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02630a2.cif
_cod_data_source_block           jav_jc_11_0m
_cod_depositor_comments
;Adding full bibliography for 7059813--7059814.cif.

 Adding full bibliography for 7059813--7059814.cif.
;
_cod_database_code               7059813
_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   0.971
_shelx_estimated_absorpt_t_min   0.809
_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:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00B,H00C), C00K(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C00A(H00A), C00E(H00E), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00L(H00K,H00L,H00M), C00M(H00N,H00O,H00P)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;
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
O001 O 0.3506(3) 0.6167(7) 0.2002(2) 0.0892(10) Uani 1 1 d . . . . .
O002 O 0.4625(2) 0.4891(7) 0.4749(3) 0.0849(9) Uani 1 1 d . . . . .
H002 H 0.480121 0.339569 0.488020 0.127 Uiso 1 1 calc GR . . . .
O003 O 0.8553(3) 0.5534(7) 0.0071(2) 0.0916(11) Uani 1 1 d . . . . .
O004 O -0.0174(3) 0.4847(7) 0.7164(2) 0.0938(10) Uani 1 1 d . . . . .
C005 C 0.5461(3) 0.4839(9) 0.1629(3) 0.0678(9) Uani 1 1 d . . . . .
C006 C 0.1576(3) 0.6767(8) 0.5105(3) 0.0688(10) Uani 1 1 d . . . . .
H006 H 0.153106 0.803351 0.461449 0.083 Uiso 1 1 calc R . . . .
C007 C 0.5541(4) 0.6791(9) 0.0927(3) 0.0734(11) Uani 1 1 d . . . . .
H007 H 0.490064 0.792590 0.081802 0.088 Uiso 1 1 calc R . . . .
C008 C 0.3406(3) 0.5014(9) 0.4328(3) 0.0688(10) Uani 1 1 d . . . . .
H008 H 0.330919 0.660665 0.394163 0.083 Uiso 1 1 calc R . . . .
C009 C 0.2517(3) 0.5034(8) 0.5128(3) 0.0649(9) Uani 1 1 d . . . . .
C00A C 0.0699(4) 0.6669(9) 0.5792(3) 0.0736(11) Uani 1 1 d . . . . .
H00A H 0.007068 0.785046 0.575645 0.088 Uiso 1 1 calc R . . . .
C00B C 0.4326(4) 0.4620(9) 0.2168(3) 0.0702(10) Uani 1 1 d . . . . .
C00C C 0.0757(4) 0.4811(9) 0.6531(3) 0.0712(10) Uani 1 1 d . . . . .
C00D C 0.7511(4) 0.5415(9) 0.0558(3) 0.0724(11) Uani 1 1 d . . . . .
C00E C 0.6554(4) 0.7078(9) 0.0386(3) 0.0749(11) Uani 1 1 d . . . . .
H00E H 0.658860 0.837784 -0.008716 0.090 Uiso 1 1 calc R . . . .
C00F C 0.3212(4) 0.2768(9) 0.3613(3) 0.0736(11) Uani 1 1 d . . . . .
H00B H 0.244984 0.300195 0.322854 0.088 Uiso 1 1 calc R . . . .
H00C H 0.315325 0.120585 0.400089 0.088 Uiso 1 1 calc R . . . .
C00G C 0.7448(4) 0.3472(9) 0.1261(4) 0.0802(12) Uani 1 1 d . . . . .
H00G H 0.809029 0.234287 0.137327 0.096 Uiso 1 1 calc R . . . .
C00H C 0.1704(4) 0.3128(9) 0.6591(3) 0.0794(12) Uani 1 1 d . . . . .
H00H H 0.176567 0.191671 0.710239 0.095 Uiso 1 1 calc R . . . .
C00I C 0.2571(4) 0.3224(9) 0.5894(3) 0.0780(12) Uani 1 1 d . . . . .
H00I H 0.320327 0.205294 0.593884 0.094 Uiso 1 1 calc R . . . .
C00J C 0.6439(4) 0.3215(9) 0.1791(3) 0.0783(12) Uani 1 1 d . . . . .
H00J H 0.641072 0.192309 0.226826 0.094 Uiso 1 1 calc R . . . .
C00K C 0.4209(4) 0.2436(9) 0.2887(3) 0.0781(12) Uani 1 1 d . . . . .
H00D H 0.497123 0.222330 0.327289 0.094 Uiso 1 1 calc R . . . .
H00F H 0.405563 0.087387 0.250599 0.094 Uiso 1 1 calc R . . . .
C00L C -0.0344(5) 0.2592(12) 0.7737(4) 0.1012(17) Uani 1 1 d . . . . .
H00K H -0.032288 0.111356 0.731049 0.152 Uiso 1 1 calc GR . . . .
H00L H -0.111086 0.267461 0.802819 0.152 Uiso 1 1 calc GR . . . .
H00M H 0.028642 0.246476 0.825968 0.152 Uiso 1 1 calc GR . . . .
C00M C 0.8681(5) 0.7562(13) -0.0632(4) 0.1056(19) Uani 1 1 d . . . . .
H00N H 0.805164 0.743916 -0.115596 0.158 Uiso 1 1 calc GR . . . .
H00O H 0.945081 0.742470 -0.091511 0.158 Uiso 1 1 calc GR . . . .
H00P H 0.862610 0.918428 -0.029846 0.158 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'
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
C00D O003 C00M 118.1(4) . . ?
C00C O004 C00L 116.8(4) . . ?
C007 C005 C00B 118.2(4) . . ?
C00J C005 C007 118.0(4) . . ?
C00J C005 C00B 123.7(4) . . ?
C009 C006 C00A 121.7(4) . . ?
C00E C007 C005 121.4(4) . . ?
O002 C008 C009 111.6(3) . . ?
O002 C008 C00F 107.8(3) . . ?
C009 C008 C00F 112.4(3) . . ?
C006 C009 C008 121.4(4) . . ?
C006 C009 C00I 117.2(3) . . ?
C00I C009 C008 121.4(4) . . ?
C00C C00A C006 119.9(4) . . ?
O001 C00B C005 120.2(4) . . ?
O001 C00B C00K 121.3(4) . . ?
C005 C00B C00K 118.5(4) . . ?
O004 C00C C00A 115.3(4) . . ?
C00H C00C O004 125.2(4) . . ?
C00H C00C C00A 119.5(4) . . ?
O003 C00D C00E 124.1(4) . . ?
O003 C00D C00G 115.9(4) . . ?
C00E C00D C00G 120.0(4) . . ?
C00D C00E C007 119.3(4) . . ?
C008 C00F C00K 114.1(4) . . ?
C00J C00G C00D 120.0(4) . . ?
C00C C00H C00I 120.2(4) . . ?
C00H C00I C009 121.5(4) . . ?
C00G C00J C005 121.3(4) . . ?
C00B C00K C00F 114.7(4) . . ?
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 C00B 1.227(5) . ?
O002 C008 1.435(5) . ?
O003 C00D 1.366(4) . ?
O003 C00M 1.428(6) . ?
O004 C00C 1.379(4) . ?
O004 C00L 1.423(7) . ?
C005 C007 1.391(6) . ?
C005 C00B 1.497(5) . ?
C005 C00J 1.383(6) . ?
C006 C009 1.380(5) . ?
C006 C00A 1.382(5) . ?
C007 C00E 1.383(5) . ?
C008 C009 1.503(5) . ?
C008 C00F 1.518(6) . ?
C009 C00I 1.392(6) . ?
C00A C00C 1.382(6) . ?
C00B C00K 1.501(6) . ?
C00C C00H 1.368(6) . ?
C00D C00E 1.380(6) . ?
C00D C00G 1.387(6) . ?
C00F C00K 1.528(5) . ?
C00G C00J 1.370(6) . ?
C00H C00I 1.383(6) . ?
