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_1552850
_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_absolute_configuration unk
_chemical_formula_moiety         'C16 H21 N O2'
_chemical_formula_sum            'C16 H21 N O2'
_chemical_formula_weight         259.34
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0450(4)
_cell_length_b                   12.4178(11)
_cell_length_c                   23.187(2)
_cell_measurement_reflns_used    1891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4325
_cell_measurement_theta_min      3.5564
_cell_volume                     1452.6(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -30.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 30

  2 omega   14.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 57

  3 omega -116.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.5714   15.0000  120.0000 115

  4 omega   96.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.5714  153.0000  144.0000 30

  5 omega  -89.00  -44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  112.0000 -180.0000 45

  6 omega -138.00 -111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000 -122.0000 -165.0000 27

  7 omega   91.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.1427 -124.0000  174.0000 26

  8 omega  139.00  173.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.1427  -25.0000  150.0000 34

  9 omega   83.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.1427   50.0000    0.0000 88

 10 omega   38.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.1427 -124.0000  174.0000 43

 11 omega  104.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.1427  112.0000 -180.0000 62

 12 omega  113.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.1427  112.0000  150.0000 61

 13 omega  -64.00   -1.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  124.0000    5.0000 63

 14 omega   20.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.5714   77.0000  -90.0000 112

 15 omega   22.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.5714   45.0000   60.0000 110
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0035843000
_diffrn_orient_matrix_UB_12      -0.0702819000
_diffrn_orient_matrix_UB_13      0.0547367000
_diffrn_orient_matrix_UB_21      0.0421168000
_diffrn_orient_matrix_UB_22      -0.1015220000
_diffrn_orient_matrix_UB_23      -0.0371428000
_diffrn_orient_matrix_UB_31      0.3022640000
_diffrn_orient_matrix_UB_32      0.0133759000
_diffrn_orient_matrix_UB_33      0.0058191000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4022
_diffrn_reflns_theta_full        70.57
_diffrn_reflns_theta_max         70.57
_diffrn_reflns_theta_min         3.81
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64206
_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    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0672
_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^)+(0.1229P)^2^+0.1773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2043
_reflns_number_gt                1811
_reflns_number_total             2322
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op8b00149_si_002.cif
_cod_data_source_block           ramelteon
_cod_database_code               1552850
_chemical_oxdiff_formula         'c16 h21 n1 o2'
_reflns_odcompleteness_completeness 99.87
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C15(H15A,H15B), C8(H8A,H8B), C7(H7A,H7B), C16(H16A,
 H16B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'