Crystal Structures of Two Important Pharmaceuticals Solved by 3D Precession Electron Diffraction Tomography
Das, Partha P.; Mugnaioli, Enrico; Nicolopoulos, Stavros; Tossi, Camilla; Gemmi, Mauro; Galanis, Athanasios; Borodi, Gheorghe; Pop, Mihaela M.; Organic Process Research & Development 22 (2018) 1365–; doi:10.1021/acs.oprd.8b00149

data_1552851
_publ_section_title
;
 Crystal Structures of Two Important Pharmaceuticals Solved by 3D
 Precession Electron Diffraction Tomography
;
_journal_issue                   10
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              1365
_journal_paper_doi               10.1021/acs.oprd.8b00149
_journal_volume                  22
_journal_year                    2018
_chemical_formula_moiety         'C26 H25 Cl N2 O3'
_chemical_formula_sum            'C26 H25 Cl N2 O3'
_chemical_formula_weight         448.93
_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_date             2017-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.118(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6270(10)
_cell_length_b                   38.007(4)
_cell_length_c                   8.5629(12)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2139
_cell_measurement_theta_min      4.6500
_cell_volume                     2359.1(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.4335
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -55.00  -29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -74.0000  160.0000 26

  2 omega  -71.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -120.0000 108

  3 omega  -61.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  125.0000   90.0000 51

  4 omega -128.00   24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839   15.0000   30.0000 152

  5 omega  -80.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  125.0000   30.0000 65

  6 omega    3.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.8839  -45.0000  -60.0000 29

  7 omega  -74.00    1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  112.0000 -180.0000 75

  8 omega   41.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000 -120.0000 35

  9 omega  124.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000    0.0000 52

 10 omega  134.00  165.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000 -120.0000 31

 11 omega  121.00  169.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   77.0000 -180.0000 48

 12 omega   81.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   77.0000 -180.0000 35

 13 omega   47.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000   90.0000 36

 14 omega   48.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  120.0000 27

 15 omega  130.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000   30.0000 40

 16 omega   84.00  173.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000  -90.0000 89

 17 omega  132.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000 -120.0000 45

 18 omega  125.00  162.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000  150.0000 37

 19 omega   47.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  -90.0000 28

 20 omega  138.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000 -120.0000 25

 21 omega   43.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000   30.0000 38

 22 omega  131.00  173.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000   60.0000 42
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1698160000
_diffrn_orient_matrix_UB_12      -0.0236652000
_diffrn_orient_matrix_UB_13      0.0213712000
_diffrn_orient_matrix_UB_21      0.1127593000
_diffrn_orient_matrix_UB_22      0.0233611000
_diffrn_orient_matrix_UB_23      0.1431036000
_diffrn_orient_matrix_UB_31      -0.0593444000
_diffrn_orient_matrix_UB_32      -0.0232100000
_diffrn_orient_matrix_UB_33      0.1222444000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8042
_diffrn_reflns_theta_full        71.35
_diffrn_reflns_theta_max         71.35
_diffrn_reflns_theta_min         4.65
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0981P)^2^+1.4416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2528
_reflns_number_gt                2954
_reflns_number_total             4468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op8b00149_si_003.cif
_cod_data_source_block           tolvaptan
_cod_original_cell_volume        2359.1(5)
_cod_database_code               1552851
_chemical_oxdiff_formula         'c26 h25 cl1 n2 o3'
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2. Uiso/Uaniso restraints and constraints
Uanis(O3) = Uanis(O3A)
3. Others
 Sof(O3A)=1-FVAR(1)
 Sof(O3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C23(H23)
4.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C24(H24A,H24B), C25(H25A,H25B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C21(H21), C14(H14), C10(H10), C18(H18), C13(H13), C19(H19), C6(H6),
 C5(H5), C3(H3), C4(H4)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C1(H1A,H1B,H1C)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'