Structural reasons for the formation of multicomponent products and the influence of high pressure
Konieczny, Krzysztof A.; Bakowicz, Julia; Paliwoda, Damian; Warren, Mark R.; Ciesielski, Arkadiusz; Cyrański, Michał K.; Turowska-Tyrk, Ilona; Acta Crystallographica Section B 77 (2021) –; doi:10.1107/S2052520621004492

data_2108829
_publ_section_title
;
 Structural reasons for the formation of multicomponent products and the
 influence of high pressure
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520621004492
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H26.67 O3, C8 H12 N'
_chemical_formula_sum            'C31 H39 N O3'
_chemical_formula_weight         473.63
_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   mixed
_audit_creation_date             2020-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9560(5)
_cell_length_b                   13.3207(11)
_cell_length_c                   31.89(3)
_cell_measurement_pressure       1500000
_cell_measurement_reflns_used    2230
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.7830
_cell_measurement_theta_min      3.0140
_cell_volume                     2530(2)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'Diamond Light Source, beamline I-19'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_pressure         1500000
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.366
_diffrn_measured_fraction_theta_max 0.345
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \f    -35.00  35.00   0.20    1.00 -90.00 -20.00   0.00    --   350
  2  \w   -133.00 -85.00   0.20    1.00    --  -20.00  70.00 -24.23  240
  3  \w   -141.00 -85.00   0.20    1.00    --  -20.00  70.00 155.77  280
  4  \w   -113.00 -82.00   0.20    1.00    --   20.00  70.00 155.77  155
  5  \w   -113.00 -82.00   0.20    1.00    --   20.00  70.00 -24.23  155
  6  \w   -101.00 -41.00   0.20    1.00    --   20.00 -70.00  24.23  300
  7  \w   -102.00 -41.00   0.20    1.00    --   20.00 -70.00-155.77  305
  8  \w   -106.00 -73.00   0.20    1.00    --  -20.00 -70.00-155.77  165
  9  \w   -106.00 -73.00   0.20    1.00    --  -20.00 -70.00  24.23  165
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.366
_diffrn_reflns_Laue_measured_fraction_max 0.345
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8166
_diffrn_reflns_point_group_measured_fraction_full 0.356
_diffrn_reflns_point_group_measured_fraction_max 0.333
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.606
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scale3 AbsPack (Rigaku OD, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
The absolute configuration was assigned to agree with that of its
precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25.
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     356
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0794
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1888P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2202
_refine_ls_wR_factor_ref         0.2555
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.342
_reflns_Friedel_fraction_max     0.317
_reflns_number_gt                1070
_reflns_number_total             1824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            eb5068sup1.cif
_cod_data_source_block           1_5gpa_144huv
_cod_database_code               2108829
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C8, C8D}
{C9, C9D}
{C10, C10D}
{C13, C13D}
{C15, C15D}
{C16, C16D}
{C17, C17D}
{C21, C21P}
{C22, C22P}
{C23, C23P}
{C11, C11D}
{C12, C12D}
3. Restrained distances
 O1P-C7P
 1.407 with sigma of 0.02
 C7P-C15P
 1.633 with sigma of 0.02
 C15P-C17P
 1.52 with sigma of 0.02
 C15P-C16P
 1.521 with sigma of 0.02
 C1-C7P
 1.515 with sigma of 0.02
 C2-C15P
 1.511 with sigma of 0.02
 C7P-C8P
 1.532 with sigma of 0.02
 C11P-C14
 1.511 with sigma of 0.02
 C23-C21
 1.524 with sigma of 0.02
 C22-C21
 1.526 with sigma of 0.02
 C7-O1
 1.21 with sigma of 0.02
 C21-C6
 1.519 with sigma of 0.02
 C7-C1
 1.514 with sigma of 0.02
 C23D-C21D
 1.5 with sigma of 0.02
 C21D-C6
 1.54 with sigma of 0.02
 C7D-C1
 1.56 with sigma of 0.02
 C7D-C22D
 1.52 with sigma of 0.02
 C22D-C21D
 1.53 with sigma of 0.02
 O1D-C7D
 1.43 with sigma of 0.02
 C7-C8
 1.492 with sigma of 0.02
 C7D-C8
 1.53 with sigma of 0.02
 O1P-C15P
 2.642 with sigma of 0.04
 C7P-C17P
 2.675 with sigma of 0.04
 C7P-C16P
 2.615 with sigma of 0.04
 C17P-C16P
 2.494 with sigma of 0.04
 C6-C7P
 2.777 with sigma of 0.04
 C3-C15P
 2.767 with sigma of 0.04
 O1P-C1
 2.485 with sigma of 0.04
 C1-C15P
 2.144 with sigma of 0.04
 C2-C17P
 2.543 with sigma of 0.04
 C2-C16P
 2.596 with sigma of 0.04
 C7P-C9P
 2.514 with sigma of 0.04
 C7P-C13P
 2.545 with sigma of 0.04
 O1P-C8P
 2.302 with sigma of 0.04
 C8P-C15P
 2.659 with sigma of 0.04
 C1-C8P
 2.601 with sigma of 0.04
 C2-C7P
 2.123 with sigma of 0.04
 C10P-C14
 2.521 with sigma of 0.04
 C12P-C14
 2.501 with sigma of 0.04
 C11P-O2
 2.409 with sigma of 0.04
 C11P-O3
 2.386 with sigma of 0.04
 C22-C23
 2.491 with sigma of 0.04
 C2-C7
 2.5 with sigma of 0.04
 C7-C6
 2.504 with sigma of 0.04
 C22-C6
 2.507 with sigma of 0.04
 C23-C6
 2.547 with sigma of 0.04
 C21-C1
 2.538 with sigma of 0.04
 C23D-C6
 2.56 with sigma of 0.04
 C21D-C7D
 2.48 with sigma of 0.04
 C1-C21D
 2.422 with sigma of 0.04
 C7D-C2
 2.645 with sigma of 0.04
 C23D-C22D
 2.577 with sigma of 0.04
 C22D-C6
 2.371 with sigma of 0.04
 C1-O1
 2.364 with sigma of 0.04
 O1D-C1
 2.5 with sigma of 0.04
 O1D-C22D
 2.48 with sigma of 0.04
 C1-C8
 2.596 with sigma of 0.04
 C22D-C8
 2.53 with sigma of 0.04
 O1-C8
 2.35 with sigma of 0.04
 O1D-C8
 2.42 with sigma of 0.04
 C9-C7
 2.471 with sigma of 0.04
 C13-C7
 2.507 with sigma of 0.04
 C7D-C13
 2.532 with sigma of 0.04
 C7D-C9
 2.532 with sigma of 0.04
 C21-C5
 2.528 with sigma of 0.04
 C5-C21D
 2.645 with sigma of 0.04
4. Restrained planarity
 C14, C7P, C8P, C9P, C10P, C11P, C12P, C13P
 with sigma of 0.05
 C14, C11P, C10P, C12P, C13P, C8P, C9P
 with sigma of 0.1
 C1, C7, C8, O1
 with sigma of 0.1
 C7P, C15P, C2, C1
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
C7 \\sim C7D \\sim C7P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C15 \\sim C15D \\sim C15P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C21 \\sim C21D \\sim C21P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
O1 \\sim O1D \\sim O1P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C9 \\sim C9D \\sim C9P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C10 \\sim C10D \\sim C10P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C11 \\sim C11D \\sim C11P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C12 \\sim C12D \\sim C12P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C13 \\sim C13D \\sim C13P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C8 \\sim C8D \\sim C8P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C22 \\sim C22D \\sim C22P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C23 \\sim C23D \\sim C23P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C16 \\sim C16D \\sim C16P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C17 \\sim C17D \\sim C17P: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C6 \\sim C1: within 3A with sigma of 0.01 and sigma for terminal atoms of 0.02
C1 \\sim C2: within 3A with sigma of 0.01 and sigma for terminal atoms of 0.02
C2 \\sim C3: within 3A with sigma of 0.01 and sigma for terminal atoms of 0.02
C3 \\sim C4: within 3A with sigma of 0.01 and sigma for terminal atoms of 0.02
C4 \\sim C5: within 3A with sigma of 0.01 and sigma for terminal atoms of 0.02
C5 \\sim C6: within 3A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C21) = Uanis(C21P)
Uanis(C15) = Uanis(C15D)
Uanis(C8) = Uanis(C8D)
Uanis(C9) = Uanis(C9D)
Uanis(C10) = Uanis(C10D)
Uanis(C13) = Uanis(C13D)
Uanis(C11) = Uanis(C11D)
Uanis(C12) = Uanis(C12D)
Uanis(C22) = Uanis(C22P)
Uanis(C23) = Uanis(C23P)
Uanis(C16) = Uanis(C16D)
Uanis(C17) = Uanis(C17D)
6. Others
 1*[Sof(O1)+Sof(C7)+Sof(C8)+Sof(C9)+Sof(H9)+Sof(C10)+Sof(H10)+Sof(C11)+
 Sof(C12)+Sof(H12)+Sof(C13)+Sof(H13)+Sof(C15)+Sof(H15)+Sof(C16)+Sof(H16A)+
 Sof(H16B)+Sof(H16C)+Sof(C17)+Sof(H17A)+Sof(H17B)+Sof(H17C)+Sof(C21)+Sof(H21)+
 Sof(C22)+Sof(H22A)+Sof(H22B)+Sof(H22C)+Sof(C23)+Sof(H23A)+Sof(H23B)+Sof(H23C)]+
 1*[Sof(O1D)+Sof(C7D)+Sof(C8D)+Sof(C9D)+Sof(H9D)+Sof(C10D)+Sof(H10D)+Sof(C11D)+
 Sof(C12D)+Sof(H12D)+Sof(C13D)+Sof(H13D)+Sof(C15D)+Sof(H15D)+Sof(C16D)+
 Sof(H16D)+Sof(H16E)+Sof(H16F)+Sof(C17D)+Sof(H17D)+Sof(H17E)+Sof(H17F)+
 Sof(C21D)+Sof(H21D)+Sof(C22D)+Sof(H22D)+Sof(H22E)+Sof(C23D)+Sof(H23D)+
 Sof(H23E)+Sof(H23F)]+1*[Sof(O1P)+Sof(C7P)+Sof(C8P)+Sof(C9P)+Sof(H9P)+Sof(C10P)+
 Sof(H10P)+Sof(C11P)+Sof(C12P)+Sof(H12P)+Sof(C13P)+Sof(H13P)+Sof(C15P)+
 Sof(C16P)+Sof(H16G)+Sof(H16H)+Sof(H16I)+Sof(C17P)+Sof(H17G)+Sof(H17H)+
 Sof(H17I)+Sof(C21P)+Sof(H21P)+Sof(C22P)+Sof(H22F)+Sof(H22G)+Sof(H22H)+
 Sof(C23P)+Sof(H23G)+Sof(H23H)+Sof(H23I)]=1 with esd of 0
 Sof(O1)=Sof(C7)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(C12)=
 Sof(H12)=Sof(C13)=Sof(H13)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=
 Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C21)=Sof(H21)=Sof(C22)=
 Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(O1D)=Sof(C7D)=Sof(C8D)=Sof(C9D)=Sof(H9D)=Sof(C10D)=Sof(H10D)=Sof(C11D)=
 Sof(C12D)=Sof(H12D)=Sof(C13D)=Sof(H13D)=Sof(C15D)=Sof(H15D)=Sof(C16D)=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17D)=Sof(H17D)=Sof(H17E)=Sof(H17F)=
 Sof(C21D)=Sof(H21D)=Sof(C22D)=Sof(H22D)=Sof(H22E)=Sof(C23D)=Sof(H23D)=
 Sof(H23E)=Sof(H23F)=FVAR(2)
 Sof(O1P)=Sof(C7P)=Sof(C8P)=Sof(C9P)=Sof(H9P)=Sof(C10P)=Sof(H10P)=Sof(C11P)=
 Sof(C12P)=Sof(H12P)=Sof(C13P)=Sof(H13P)=Sof(C15P)=Sof(C16P)=Sof(H16G)=
 Sof(H16H)=Sof(H16I)=Sof(C17P)=Sof(H17G)=Sof(H17H)=Sof(H17I)=Sof(C21P)=
 Sof(H21P)=Sof(C22P)=Sof(H22F)=Sof(H22G)=Sof(H22H)=Sof(C23P)=Sof(H23G)=
 Sof(H23H)=Sof(H23I)=FVAR(3)
 Uiso(C9P)=Uiso(C10P)=Uiso(C12P)=Uiso(C13P)=FVAR(4)
7.a Free rotating group:
 C6(C1,C2,C3,H3,C4,C5,H5), C26(N1,H1A,H1B,H1C,C24,H24A,H24B,H24C,C25,H25,C27,
 H27,C28,H28,C29,H29,C30,H30,C31,H31), C8(C9,H9,C10,H10,C11,C12,H12,C13,H13),
 C8P(C9P,H9P,C10P,H10P,C11P,C12P,H12P,C13P,H13P)
7.b Ternary CH refined with riding coordinates:
 C18(H18), C15(H15), C21(H21), C15D(H15D), C21D(H21D), C21P(H21P)
7.c Secondary CH2 refined with riding coordinates:
 C22D(H22D,H22E)
7.d Me refined with riding coordinates:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C16D(H16D,H16E,H16F),
 C17D(H17D,H17E,H17F), C23D(H23D,H23E,H23F), C16P(H16G,H16H,H16I), C17P(H17G,
 H17H,H17I), C22P(H22F,H22G,H22H), C23P(H23G,H23H,H23I)
7.e Aromatic/amide H refined with riding coordinates:
 C9D(H9D), C10D(H10D), C12D(H12D), C13D(H13D)
;
_shelx_res_checksum              3403
_shelx_hkl_checksum              69127
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2108829