#------------------------------------------------------------------------------
#$Date: 2021-06-04 03:58:21 +0300 (Fri, 04 Jun 2021) $
#$Revision: 265750 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/87/4518727.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_4518727
loop_
_publ_author_name
'Yu, Hongmei'
'Zhang, Yong'
'Xing, Cheng'
'Wang, Ying'
'Zhang, Hailu'
'Gong, Ningbo'
'Lu, Yang'
'Du, Guanhua'
_publ_section_title
;
 Venlafaxine Caffeic Acid Salt: Synthesis, Structural Characterization,
 and Hypoglycemic Effect Analysis
;
_journal_issue                   21
_journal_name_full               'ACS Omega'
_journal_page_first              13895
_journal_page_last               13903
_journal_paper_doi               10.1021/acsomega.1c01581
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C17 H27 N1 O2. C9 H8 O4'
_chemical_formula_sum            'C26 H35 N O6'
_chemical_formula_weight         457.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 102.7178(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3663(2)
_cell_length_b                   10.80081(18)
_cell_length_c                   17.0804(3)
_cell_measurement_reflns_used    4264
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.857
_cell_measurement_theta_min      3.817
_cell_volume                     2405.35(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    ORTEPII(Johnson,1976)andPLUTON(Spek,1990)
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MicroMax 002+'
_diffrn_measurement_method       /w/k
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27484
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.857
_diffrn_reflns_theta_max         66.857
_diffrn_reflns_theta_min         3.817
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995).  '
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.042
_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     304
_refine_ls_number_reflns         4264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0451
_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)+(0.0626P)²+0.8494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3609
_reflns_number_total             4264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c01581_si_002.cif
_cod_data_source_block           6030
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4518727.cif.
;
_cod_original_cell_volume        2405.33(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518727
_shelx_shelxl_version_number     2016/6
_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_min   0.819
_shelx_estimated_absorpt_t_max   0.944
_exptl_absorpt_special_details   sadabs
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_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
N1 N 0.67047(10) 0.85854(13) 0.15262(8) 0.0404(3) Uani 1 1 d . . . . .
H1 H 0.693475 0.819713 0.107791 0.049 Uiso 1 1 calc R U . . .
O1 O 0.46873(12) 0.48317(14) 0.39552(8) 0.0651(4) Uani 1 1 d . . . . .
O2 O 0.42655(10) 0.82569(15) -0.01913(8) 0.0620(4) Uani 1 1 d . . . . .
H2A H 0.478260 0.797943 -0.031168 0.093 Uiso 1 1 calc R U . . .
O3 O 0.62727(9) 0.78511(13) 0.95502(7) 0.0546(3) Uani 1 1 d . . . . .
O4 O 0.75736(9) 0.71640(13) 1.04801(7) 0.0525(3) Uani 1 1 d . . . . .
O5 O 1.11217(9) 0.39319(15) 0.82580(7) 0.0598(4) Uani 1 1 d . . . . .
H5A H 1.136277 0.376950 0.873094 0.090 Uiso 1 1 calc R U . . .
O6 O 0.98733(9) 0.32776(12) 0.69043(7) 0.0503(3) Uani 1 1 d . . . . .
H6A H 0.943557 0.316386 0.649180 0.075 Uiso 1 1 calc R U . . .
C1 C 0.48965(12) 0.66638(15) 0.18470(9) 0.0378(4) Uani 1 1 d . . . . .
C2 C 0.51259(12) 0.54106(16) 0.19329(10) 0.0424(4) Uani 1 1 d . . . . .
H2 H 0.533730 0.499937 0.151894 0.051 Uiso 1 1 calc R U . . .
C3 C 0.50508(13) 0.47488(16) 0.26154(11) 0.0446(4) Uani 1 1 d . . . . .
H3 H 0.520130 0.390737 0.265272 0.054 Uiso 1 1 calc R U . . .
C4 C 0.47493(12) 0.53567(17) 0.32398(10) 0.0441(4) Uani 1 1 d . . . . .
C5 C 0.44815(13) 0.65935(17) 0.31559(10) 0.0459(4) Uani 1 1 d . . . . .
H5 H 0.424993 0.699605 0.356367 0.055 Uiso 1 1 calc R U . . .
C6 C 0.45543(13) 0.72342(16) 0.24746(10) 0.0429(4) Uani 1 1 d . . . . .
H6 H 0.437155 0.806632 0.243062 0.052 Uiso 1 1 calc R U . . .
C7 C 0.50431(12) 0.73838(16) 0.11149(9) 0.0390(4) Uani 1 1 d . . . . .
H7 H 0.550996 0.689220 0.087041 0.047 Uiso 1 1 calc R U . . .
C8 C 0.40380(13) 0.75507(18) 0.04558(10) 0.0465(4) Uani 1 1 d . . . . .
C9 C 0.36067(19) 0.6300(2) 0.01510(13) 0.0713(6) Uani 1 1 d . . . . .
H9A H 0.347726 0.581450 0.059630 0.086 Uiso 1 1 calc R U . . .
H9B H 0.410626 0.585924 -0.007842 0.086 Uiso 1 1 calc R U . . .
C10 C 0.2598(3) 0.6443(3) -0.04914(16) 0.1031(11) Uani 1 1 d . . . . .
H10A H 0.274407 0.684493 -0.096189 0.124 Uiso 1 1 calc R U . . .
H10B H 0.231846 0.563000 -0.065061 0.124 Uiso 1 1 calc R U . . .
C11 C 0.1816(2) 0.7193(4) -0.01839(19) 0.1053(11) Uani 1 1 d . . . . .
H11A H 0.121290 0.730844 -0.061268 0.126 Uiso 1 1 calc R U . . .
H11B H 0.160884 0.674421 0.024635 0.126 Uiso 1 1 calc R U . . .
C12 C 0.22315(16) 0.8427(3) 0.01185(16) 0.0850(8) Uani 1 1 d . . . . .
H12A H 0.172799 0.885951 0.034804 0.102 Uiso 1 1 calc R U . . .
H12B H 0.235626 0.891685 -0.032651 0.102 Uiso 1 1 calc R U . . .
C13 C 0.32253(14) 0.8301(2) 0.07508(13) 0.0629(6) Uani 1 1 d . . . . .
H13A H 0.308016 0.790334 0.122277 0.075 Uiso 1 1 calc R U . . .
H13B H 0.349486 0.911998 0.090661 0.075 Uiso 1 1 calc R U . . .
C14 C 0.55561(12) 0.86440(16) 0.13172(11) 0.0435(4) Uani 1 1 d . . . . .
H14A H 0.534181 0.919154 0.086093 0.052 Uiso 1 1 calc R U . . .
H14B H 0.531997 0.899907 0.176600 0.052 Uiso 1 1 calc R U . . .
C15 C 0.71077(16) 0.9875(2) 0.16169(16) 0.0697(6) Uani 1 1 d . . . . .
H15A H 0.681810 1.034129 0.114258 0.104 Uiso 1 1 calc R U . . .
H15B H 0.784097 0.986010 0.169316 0.104 Uiso 1 1 calc R U . . .
H15C H 0.692385 1.025550 0.207345 0.104 Uiso 1 1 calc R U . . .
C16 C 0.71299(15) 0.7872(2) 0.22615(11) 0.0579(5) Uani 1 1 d . . . . .
H16A H 0.689098 0.821978 0.270433 0.087 Uiso 1 1 calc R U . . .
H16B H 0.786535 0.790610 0.237236 0.087 Uiso 1 1 calc R U . . .
H16C H 0.690983 0.702577 0.218594 0.087 Uiso 1 1 calc R U . . .
C17 C 0.5125(2) 0.3659(2) 0.41453(16) 0.0851(8) Uani 1 1 d . . . . .
H17A H 0.472717 0.304822 0.380376 0.128 Uiso 1 1 calc R U . . .
H17B H 0.513191 0.346948 0.469567 0.128 Uiso 1 1 calc R U . . .
H17C H 0.581398 0.365742 0.406672 0.128 Uiso 1 1 calc R U . . .
C18 C 0.97279(12) 0.49145(16) 0.87259(9) 0.0389(4) Uani 1 1 d . . . . .
H18 H 1.017131 0.514697 0.920271 0.047 Uiso 1 1 calc R U . . .
C19 C 1.01097(12) 0.42521(16) 0.81637(9) 0.0392(4) Uani 1 1 d . . . . .
C20 C 0.94560(12) 0.39090(15) 0.74397(9) 0.0390(4) Uani 1 1 d . . . . .
C21 C 0.84272(13) 0.42219(17) 0.73121(10) 0.0464(4) Uani 1 1 d . . . . .
H21 H 0.798323 0.398895 0.683578 0.056 Uiso 1 1 calc R U . . .
C22 C 0.80500(13) 0.48740(17) 0.78806(10) 0.0467(4) Uani 1 1 d . . . . .
H22 H 0.735571 0.506851 0.778292 0.056 Uiso 1 1 calc R U . . .
C23 C 0.86947(12) 0.52438(15) 0.85974(9) 0.0376(4) Uani 1 1 d . . . . .
C24 C 0.83288(12) 0.59733(15) 0.92038(9) 0.0395(4) Uani 1 1 d . . . . .
H24 H 0.878550 0.607458 0.969584 0.047 Uiso 1 1 calc R U . . .
C25 C 0.74193(12) 0.65019(16) 0.91256(9) 0.0419(4) Uani 1 1 d . . . . .
H25 H 0.695943 0.642176 0.863321 0.050 Uiso 1 1 calc R U . . .
C26 C 0.70747(12) 0.72140(16) 0.97631(9) 0.0401(4) Uani 1 1 d . . . . .
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'
N N 0.0311 0.0180 '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
C16 N1 C15 109.70(16) . . ?
C16 N1 C14 114.01(13) . . ?
C15 N1 C14 108.26(14) . . ?
C4 O1 C17 118.54(16) . . ?
C2 C1 C6 116.78(15) . . ?
C2 C1 C7 121.31(14) . . ?
C6 C1 C7 121.88(15) . . ?
C1 C2 C3 122.33(15) . . ?
C4 C3 C2 119.27(16) . . ?
O1 C4 C5 115.39(15) . . ?
O1 C4 C3 125.23(16) . . ?
C5 C4 C3 119.38(16) . . ?
C6 C5 C4 120.60(16) . . ?
C5 C6 C1 121.53(16) . . ?
C1 C7 C14 113.69(13) . . ?
C1 C7 C8 113.92(13) . . ?
C14 C7 C8 109.38(14) . . ?
O2 C8 C9 109.86(16) . . ?
O2 C8 C13 105.06(15) . . ?
C9 C8 C13 110.00(17) . . ?
O2 C8 C7 108.86(13) . . ?
C9 C8 C7 110.27(16) . . ?
C13 C8 C7 112.64(15) . . ?
C8 C9 C10 111.1(2) . . ?
C11 C10 C9 111.7(2) . . ?
C12 C11 C10 111.5(2) . . ?
C11 C12 C13 111.5(2) . . ?
C12 C13 C8 112.7(2) . . ?
N1 C14 C7 113.64(13) . . ?
C19 C18 C23 121.76(15) . . ?
O5 C19 C18 123.68(15) . . ?
O5 C19 C20 116.46(14) . . ?
C18 C19 C20 119.82(14) . . ?
O6 C20 C21 123.93(15) . . ?
O6 C20 C19 117.40(14) . . ?
C21 C20 C19 118.67(14) . . ?
C22 C21 C20 121.12(15) . . ?
C21 C22 C23 120.90(15) . . ?
C22 C23 C18 117.70(15) . . ?
C22 C23 C24 122.46(15) . . ?
C18 C23 C24 119.83(14) . . ?
C25 C24 C23 126.99(15) . . ?
C24 C25 C26 125.12(15) . . ?
O3 C26 O4 122.63(15) . . ?
O3 C26 C25 116.93(14) . . ?
O4 C26 C25 120.44(14) . . ?
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
N1 C16 1.476(2) . ?
N1 C15 1.489(3) . ?
N1 C14 1.499(2) . ?
O1 C4 1.366(2) . ?
O1 C17 1.403(3) . ?
O2 C8 1.430(2) . ?
O3 C26 1.258(2) . ?
O4 C26 1.2601(19) . ?
O5 C19 1.3709(19) . ?
O6 C20 1.3554(19) . ?
C1 C2 1.389(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.521(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.386(2) . ?
C4 C5 1.382(3) . ?
C5 C6 1.376(2) . ?
C7 C14 1.529(2) . ?
C7 C8 1.562(2) . ?
C8 C9 1.516(3) . ?
C8 C13 1.527(3) . ?
C9 C10 1.547(3) . ?
C10 C11 1.506(5) . ?
C11 C12 1.492(5) . ?
C12 C13 1.522(3) . ?
C18 C19 1.382(2) . ?
C18 C23 1.396(2) . ?
C19 C20 1.398(2) . ?
C20 C21 1.386(2) . ?
C21 C22 1.382(2) . ?
C22 C23 1.392(2) . ?
C23 C24 1.468(2) . ?
C24 C25 1.323(2) . ?
C25 C26 1.487(2) . ?
