C(21)-Di- and monofluorinated scaffold for thevinol/orvinol-based opioid receptor ligands.
Zelentsova, Maria V.; Sandulenko, Irina V.; Ambartsumyan, Asmik A.; Danshina, Anastasia A.; Moiseev, Sergey K.; Organic & biomolecular chemistry 21 (2023) 9091–9100; doi:10.1039/d3ob01577g

data_7159616
_publ_section_title
;
 C(21)-Di- and monofluorinated scaffold for thevinol/orvinol-based opioid
 receptor ligands.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9091
_journal_page_last               9100
_journal_paper_doi               10.1039/d3ob01577g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C24 H29 F2 N O4, C H4 O'
_chemical_formula_sum            'C25 H33 F2 N O5'
_chemical_formula_weight         465.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-09-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-11 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.636(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   40.487(3)
_cell_length_b                   7.3959(4)
_cell_length_c                   7.5817(5)
_cell_measurement_reflns_used    6129
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.70
_cell_volume                     2259.3(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20675
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.990
_diffrn_reflns_theta_min         2.022
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1436 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.7853.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5921
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0729
_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^)+(0.0558P)^2^+5.6167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1674
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4773
_reflns_number_total             5921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01577g2.cif
_cod_data_source_block           34
_cod_depositor_comments
'Adding full bibliography for 7159615--7159624.cif.'
_cod_original_cell_volume        2259.3(2)
_cod_database_code               7159616
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4'-C20 \\sim O4-C20
 with sigma of 0.02
 C22-C20 \\sim C22'-C20
 with sigma of 0.02
 F2'-C21' \\sim F2-C21
 with sigma of 0.02
 F1'-C21' \\sim F1-C21
 with sigma of 0.02
 O1-C23 \\sim O1-C23'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O4') = Uanis(O4)
Uanis(C22') = Uanis(C22)
Uanis(F1') = Uanis(F1)
Uanis(C21) = Uanis(C21')
Uanis(F2') = Uanis(F2)
Uanis(C23) = Uanis(C23')
4. Others
 Sof(F1)=Sof(F2)=Sof(O4)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=1-FVAR(1)
 Sof(F1')=Sof(F2')=Sof(O4')=Sof(C21')=Sof(H21')=Sof(C22')=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=FVAR(1)
 Sof(C23')=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(2)
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(2)
 Fixed Sof: O1S(0.5) H1S(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) O2S(0.5)
 H2S(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5)
5.a Riding coordinates:
 O4(H4), O1S(H1S), O2S(H2S)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C21(H21), C21'(H21')
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C22'(H22D,H22E,H22F), C23'(H23D,H23E,H23F), C1S(H1SA,H1SB,H1SC),
 C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              17045
_olex2_submission_special_instructions 'No special instructions were received'