data_cu_dm16814_0m
_audit_creation_date              2016-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C17 H22 O4, H2 O'
_chemical_formula_sum             'C17 H24 O5'
_chemical_formula_weight          308.36
_chemical_absolute_configuration  rmad
_chemical_melting_point           ?
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'

_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.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                    9.3465(3)
_cell_length_b                    9.3699(3)
_cell_length_c                    18.6281(6)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1631.37(9)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     5715
_cell_measurement_temperature     296
_cell_measurement_theta_max       69.25
_cell_measurement_theta_min       4.75
_shelx_estimated_absorpt_T_max    0.929
_shelx_estimated_absorpt_T_min    0.864
_exptl_absorpt_coefficient_mu     0.751
_exptl_absorpt_correction_T_max   0.7533
_exptl_absorpt_correction_T_min   0.4893
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1078 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.6495.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_diffrn     1.255
_exptl_crystal_density_meas       .
_exptl_crystal_density_method     ?
_exptl_crystal_description        'block'
_exptl_crystal_F_000              664
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.1
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0316
_diffrn_reflns_av_unetI/netI      0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_number             10793
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full         67.679
_diffrn_reflns_theta_max          69.906
_diffrn_reflns_theta_min          4.748
_diffrn_ambient_temperature       296
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.952
_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_source                    ?
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.706
_reflns_Friedel_fraction_full     0.954
_reflns_Friedel_fraction_max      0.924
_reflns_number_gt                 2816
_reflns_number_total              2906
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection        ?
_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   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.131
_refine_diff_density_min          -0.180
_refine_diff_density_rms          0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.15(7)
_refine_ls_extinction_coef        0.0035(6)
_refine_ls_extinction_expression  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method      'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref    1.069
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      208
_refine_ls_number_reflns          2906
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0328
_refine_ls_R_factor_gt            0.0318
_refine_ls_restrained_S_all       1.069
_refine_ls_shift/su_max           0.003
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0522P)²+0.1340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0871
_refine_ls_wR_factor_ref          0.0881
_refine_special_details           ?
_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, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C4(H4A), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
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
 O1 O 0.54746(14) 0.45512(13) 0.44690(7) 0.0422(3) Uani 1 1 d . . . . .
 O2 O 0.58904(16) 0.17733(14) 0.49844(7) 0.0440(3) Uani 1 1 d . . . . .
 O3 O 0.68662(19) 0.17858(16) 0.61075(7) 0.0526(4) Uani 1 1 d . . . . .
 O4 O 0.6184(2) 0.29811(17) 0.20841(7) 0.0598(4) Uani 1 1 d . . . . .
 H4 H 0.642974 0.228022 0.185104 0.090 Uiso 1 1 calc GR . . . .
 C2 C 0.6596(2) 0.5057(2) 0.49560(11) 0.0437(4) Uani 1 1 d . . . . .
 C3 C 0.6962(2) 0.39159(19) 0.55098(9) 0.0400(4) Uani 1 1 d . . . . .
 H3 H 0.784789 0.421639 0.574731 0.048 Uiso 1 1 calc R . . . .
 C4 C 0.7055(2) 0.2320(2) 0.54062(10) 0.0420(4) Uani 1 1 d . . . . .
 H4A H 0.798269 0.203728 0.520654 0.050 Uiso 1 1 calc R . . . .
 C5 C 0.6295(2) 0.0958(2) 0.37782(10) 0.0405(4) Uani 1 1 d . . . . .
 C6 C 0.6345(2) 0.1258(2) 0.30455(10) 0.0433(4) Uani 1 1 d . . . . .
 H6 H 0.651475 0.052363 0.272037 0.052 Uiso 1 1 calc R . . . .
 C7 C 0.6146(2) 0.2639(2) 0.27955(10) 0.0433(4) Uani 1 1 d . . . . .
 C8 C 0.5897(2) 0.3740(2) 0.32752(10) 0.0423(4) Uani 1 1 d . . . . .
 H8 H 0.576821 0.466707 0.310887 0.051 Uiso 1 1 calc R . . . .
 C9 C 0.5870(3) 0.6221(2) 0.54240(12) 0.0583(6) Uani 1 1 d . . . . .
 H9A H 0.645273 0.707781 0.543119 0.070 Uiso 1 1 calc R . . . .
 H9B H 0.493945 0.646178 0.522796 0.070 Uiso 1 1 calc R . . . .
 C10 C 0.5705(3) 0.5620(2) 0.61939(11) 0.0563(6) Uani 1 1 d . . . . .
 H10A H 0.647782 0.593631 0.650315 0.068 Uiso 1 1 calc R . . . .
 H10B H 0.479722 0.589524 0.640448 0.068 Uiso 1 1 calc R . . . .
 C11 C 0.5776(2) 0.4017(2) 0.60620(10) 0.0442(4) Uani 1 1 d . . . . .
 H11 H 0.488116 0.373031 0.582850 0.053 Uiso 1 1 calc R . . . .
 C12 C 0.6187(2) 0.2851(2) 0.65895(10) 0.0479(5) Uani 1 1 d . . . . .
 C13 C 0.4927(3) 0.2115(3) 0.69407(13) 0.0689(7) Uani 1 1 d . . . . .
 H13A H 0.424082 0.185469 0.658027 0.103 Uiso 1 1 calc GR . . . .
 H13B H 0.448953 0.275067 0.727995 0.103 Uiso 1 1 calc GR . . . .
 H13C H 0.525147 0.127226 0.718464 0.103 Uiso 1 1 calc GR . . . .
 C14 C 0.7291(3) 0.3287(3) 0.71478(12) 0.0630(6) Uani 1 1 d . . . . .
 H14A H 0.763395 0.245352 0.739331 0.094 Uiso 1 1 calc GR . . . .
 H14B H 0.685975 0.392586 0.748751 0.094 Uiso 1 1 calc GR . . . .
 H14C H 0.807713 0.375700 0.691487 0.094 Uiso 1 1 calc GR . . . .
 C15 C 0.7855(3) 0.5598(2) 0.45202(14) 0.0589(6) Uani 1 1 d . . . . .
 H15A H 0.829257 0.481386 0.427145 0.088 Uiso 1 1 calc GR . . . .
 H15B H 0.854184 0.603129 0.483501 0.088 Uiso 1 1 calc GR . . . .
 H15C H 0.752617 0.629046 0.417809 0.088 Uiso 1 1 calc GR . . . .
 C16 C 0.6481(3) -0.0546(2) 0.40476(12) 0.0557(6) Uani 1 1 d . . . . .
 H16A H 0.559179 -0.088232 0.424256 0.084 Uiso 1 1 calc GR . . . .
 H16B H 0.720215 -0.056245 0.441433 0.084 Uiso 1 1 calc GR . . . .
 H16C H 0.676694 -0.115193 0.365760 0.084 Uiso 1 1 calc GR . . . .
 C4A C 0.6039(2) 0.20690(19) 0.42598(10) 0.0381(4) Uani 1 1 d . . . . .
 C8A C 0.5840(2) 0.34543(19) 0.40020(10) 0.0378(4) Uani 1 1 d . . . . .
 O5 O 0.6930(2) 0.09727(16) 0.11271(9) 0.0588(4) Uani 1 1 d . . . . .
 H5A H 0.747139 0.025777 0.119833 0.088 Uiso 1 1 d G . . . .
 H5B H 0.616312 0.069828 0.092415 0.088 Uiso 1 1 d G . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 O1 C2 1.465(2) . ?
 O1 C8A 1.389(2) . ?
 O2 C4 1.437(2) . ?
 O2 C4A 1.385(2) . ?
 O3 C4 1.410(2) . ?
 O3 C12 1.485(3) . ?
 O4 H4 0.8200 . ?
 O4 C7 1.364(2) . ?
 C2 C3 1.524(3) . ?
 C2 C9 1.553(3) . ?
 C2 C15 1.516(3) . ?
 C3 H3 0.9800 . ?
 C3 C4 1.511(3) . ?
 C3 C11 1.516(3) . ?
 C4 H4A 0.9800 . ?
 C5 C6 1.394(3) . ?
 C5 C16 1.506(3) . ?
 C5 C4A 1.395(3) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.388(3) . ?
 C7 C8 1.385(3) . ?
 C8 H8 0.9300 . ?
 C8 C8A 1.381(3) . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C9 C10 1.549(3) . ?
 C10 H10A 0.9700 . ?
 C10 H10B 0.9700 . ?
 C10 C11 1.523(3) . ?
 C11 H11 0.9800 . ?
 C11 C12 1.520(3) . ?
 C12 C13 1.514(3) . ?
 C12 C14 1.521(3) . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?
 C15 H15A 0.9600 . ?
 C15 H15B 0.9600 . ?
 C15 H15C 0.9600 . ?
 C16 H16A 0.9600 . ?
 C16 H16B 0.9600 . ?
 C16 H16C 0.9600 . ?
 C4A C8A 1.396(3) . ?
 O5 H5A 0.8499 . ?
 O5 H5B 0.8501 . ?

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
 C8A O1 C2 116.82(15) . . ?
 C4A O2 C4 112.68(14) . . ?
 C4 O3 C12 112.05(15) . . ?
 C7 O4 H4 109.5 . . ?
 O1 C2 C3 110.66(15) . . ?
 O1 C2 C9 105.20(17) . . ?
 O1 C2 C15 109.37(17) . . ?
 C3 C2 C9 102.17(16) . . ?
 C15 C2 C3 115.01(18) . . ?
 C15 C2 C9 113.87(18) . . ?
 C2 C3 H3 107.1 . . ?
 C4 C3 C2 128.37(16) . . ?
 C4 C3 H3 107.1 . . ?
 C4 C3 C11 101.00(15) . . ?
 C11 C3 C2 104.55(16) . . ?
 C11 C3 H3 107.1 . . ?
 O2 C4 C3 112.29(16) . . ?
 O2 C4 H4A 111.5 . . ?
 O3 C4 O2 106.59(15) . . ?
 O3 C4 C3 103.05(15) . . ?
 O3 C4 H4A 111.5 . . ?
 C3 C4 H4A 111.5 . . ?
 C6 C5 C16 120.74(17) . . ?
 C6 C5 C4A 118.99(17) . . ?
 C4A C5 C16 120.26(17) . . ?
 C5 C6 H6 119.6 . . ?
 C7 C6 C5 120.80(18) . . ?
 C7 C6 H6 119.6 . . ?
 O4 C7 C6 122.82(17) . . ?
 O4 C7 C8 117.13(18) . . ?
 C8 C7 C6 120.06(18) . . ?
 C7 C8 H8 120.2 . . ?
 C8A C8 C7 119.64(18) . . ?
 C8A C8 H8 120.2 . . ?
 C2 C9 H9A 110.1 . . ?
 C2 C9 H9B 110.1 . . ?
 H9A C9 H9B 108.4 . . ?
 C10 C9 C2 107.93(17) . . ?
 C10 C9 H9A 110.1 . . ?
 C10 C9 H9B 110.1 . . ?
 C9 C10 H10A 111.4 . . ?
 C9 C10 H10B 111.4 . . ?
 H10A C10 H10B 109.3 . . ?
 C11 C10 C9 101.83(16) . . ?
 C11 C10 H10A 111.4 . . ?
 C11 C10 H10B 111.4 . . ?
 C3 C11 C10 101.70(17) . . ?
 C3 C11 H11 107.8 . . ?
 C3 C11 C12 102.03(16) . . ?
 C10 C11 H11 107.8 . . ?
 C12 C11 C10 128.03(18) . . ?
 C12 C11 H11 107.8 . . ?
 O3 C12 C11 101.58(15) . . ?
 O3 C12 C13 106.7(2) . . ?
 O3 C12 C14 107.72(19) . . ?
 C11 C12 C14 114.9(2) . . ?
 C13 C12 C11 114.2(2) . . ?
 C13 C12 C14 110.79(19) . . ?
 C12 C13 H13A 109.5 . . ?
 C12 C13 H13B 109.5 . . ?
 C12 C13 H13C 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?
 C12 C14 H14A 109.5 . . ?
 C12 C14 H14B 109.5 . . ?
 C12 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 C2 C15 H15A 109.5 . . ?
 C2 C15 H15B 109.5 . . ?
 C2 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 C5 C16 H16A 109.5 . . ?
 C5 C16 H16B 109.5 . . ?
 C5 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 O2 C4A C5 119.64(16) . . ?
 O2 C4A C8A 120.51(16) . . ?
 C5 C4A C8A 119.70(17) . . ?
 O1 C8A C4A 120.34(16) . . ?
 C8 C8A O1 118.68(16) . . ?
 C8 C8A C4A 120.81(17) . . ?
 H5A O5 H5B 109.5 . . ?

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
 O4 H4 O5 0.82 1.88 2.684(2) 166.1 .
 O5 H5A O3 0.85 2.02 2.819(2) 156.4 2_654
 O5 H5B O1 0.85 2.01 2.839(2) 165.1 3_645

_shelx_SHELXL_version_number      '2016/6'
_olex2_submission_special_instructions 'No special instructions were received'
