The Devil is in the Detail: A Rare H-Bonding Motif in New Forms of Docetaxel
Vella-Zarb, Liana; Dinnebier, Robert E.; Baisch, Ulrich; Crystal Growth & Design 13 (2013) 4402–; doi:10.1021/cg400814a

data_4510773
_publ_section_title
;
 The Devil is in the Detail: A Rare H-Bonding Motif in New Forms of
 Docetaxel
;
_journal_issue                   10
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              4402
_journal_paper_doi               10.1021/cg400814a
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C43 H53 N O14, C2 H7 O2'
_chemical_formula_sum            'C45 H60 N O16'
_chemical_formula_weight         870.94
_chemical_name_systematic        'Docetaxel hydrate ethanol solvate'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2013-05-18
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.942(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.608(3)
_cell_length_b                   8.6626(19)
_cell_length_c                   20.353(4)
_cell_measurement_reflns_used    9144
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.55
_cell_measurement_theta_min      2.95
_cell_volume                     2195.9(8)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XM, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device       ' 'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.688900
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26748
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.739
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.687
_diffrn_reflns_theta_min         1.013
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0939 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The \l/2 correction factor is 0.0015.
;
_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    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             930
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         11926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0499
_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/[\s^2^(Fo^2^)+(0.0933P)^2^+0.5162P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.592
_reflns_number_gt                11129
_reflns_number_total             11926
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg400814a_si_002.cif
_cod_data_source_block           DoceEtW
_cod_original_cell_volume        2196.0(8)
_cod_database_code               4510773
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: C911(0.5) H91A(0.5) H91B(0.5) C912(0.5) H91C(0.5) H91D(0.5)
 H91E(0.5) C913(0.5) H91F(0.5) H91G(0.5) H91H(0.5) C914(0.5) H91I(0.5) H91J(0.5)
3.a Free rotating group:
 O900(H90A,H90B)
3.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C7(H7), C13(H13), C47(H47), C45(H45)
3.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C6(H6A,H6B), C20(H20A,H20B), C911(H91A,H91B), C914(H91I,H91J)
3.d Aromatic/amide H refined with riding coordinates:
 N54(H54), C49(H49), C52(H52), C51(H51), C53(H53), C50(H50), C33(H33),
 C29(H29), C32(H32), C31(H31), C30(H30)
3.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C37(H37A,H37B,
 H37C), C17(H17A,H17B,H17C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C59(H59A,
 H59B,H59C), C912(H91C,H91D,H91E), C913(H91F,H91G,H91H)
3.f Idealised tetrahedral OH refined as rotating group:
 O22(H22), O23(H23), O38(H38), O46(H46)
;
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.990
_shelx_hkl_checksum              64516
_shelx_res_checksum              83452
_shelxl_version_number           2012-9