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_4510771
_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_absolute_configuration unk
_chemical_formula_moiety         'C43 H53 N O14, 3(H2 O)'
_chemical_formula_sum            'C43 H59 N O17'
_chemical_formula_weight         861.91
_chemical_name_systematic        'Docetaxel trihydrate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2012-12-24
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.594(2)
_cell_length_b                   12.644(3)
_cell_length_c                   39.717(10)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.74
_cell_volume                     4315.7(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      120.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_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  0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            39684
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.465
_diffrn_reflns_theta_min         2.159
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1564 before and 0.0683 after correction.
The Ratio of minimum to maximum transmission is 0.9236.
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    1.327
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 2729 quotients [(I+)-I(-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         9563
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0603P)^2^+3.0907P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                7539
_reflns_number_total             9563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg400814a_si_002.cif
_cod_data_source_block           doce3W
_cod_original_cell_volume        4315.8(18)
_cod_database_code               4510771
_diffrn_reflns_sigmai/neti       0.0874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H51 of C51, H30 of C30, H47 of C47, H49 of C49, H50 of C50, H53 of C53,
  {H6A,H6B} of C6, H7 of C7, H10 of C10, H31 of C31, H29 of C29, H52 of C52,
  H32 of C32, H5 of C5, H45 of C45, H54 of N54, H3 of C3, H33 of C33, H2 of C2,
  H13 of C13, {H14A,H14B} of C14, {H20A,H20B} of C20
 At 1.5 times of:
  H38 of O38, {H59A,H59B,H59C} of C59, {H61A,H61B,H61C} of C61, H46 of O46,
  {H37A,H37B,H37C} of C37, {H10C,H10D,H10E,H10F} of O101, {H10A,H10B} of O102,
  H22 of O22, {H16A,H16B,H16C} of C16, {H17A,H17B,H17C} of C17, {H18A,H18B,
  H18C} of C18, {H19A,H19B,H19C} of C19, {H60A,H60B,H60C} of C60
2. Restrained distances
 O100-H10E = O100-H10F
 0.83 with sigma of 0.02
 H23-O23
 0.85 with sigma of 0.02
3.a Riding coordinates:
 N54(H54), O22(H22), O57(O100,O101,H10C,H10D), O101(H10E,H10F), O102(H10A,H10B)
3.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C13(H13), C45(H45), C47(H47)
3.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C20(H20A,H20B)
3.d Aromatic/amide H refined with riding coordinates:
 C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C49(H49), C50(H50),
 C51(H51), C52(H52), C53(H53)
3.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C37(H37A,H37B,H37C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C61(H61A,
 H61B,H61C)
3.f Idealised tetrahedral OH refined as rotating group:
 O38(H38), O46(H46)
;
_shelxl_version_number           2012-4