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_7159617
_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         'C23 H26 F2 N2 O4'
_chemical_formula_sum            'C23 H26 F2 N2 O4'
_chemical_formula_weight         432.46
_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             2023-09-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7726(4)
_cell_length_b                   11.5067(6)
_cell_length_c                   22.6755(10)
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.52
_cell_volume                     2028.03(17)
_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)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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  0.0914
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26533
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         1.985
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1535 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.8477.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5347
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0528P)^2^+1.8343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4287
_reflns_number_total             5347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01577g2.cif
_cod_data_source_block           40
_cod_depositor_comments
'Adding full bibliography for 7159615--7159624.cif.'
_cod_database_code               7159617
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.979
_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
 N1-C17 \\sim N1-C17'
 with sigma of 0.02
 N2-C17 \\sim N2'-C17'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N2) = Uanis(N2')
Uanis(C17) = Uanis(C17')
4. Others
 Sof(N2')=Sof(C17')=1-FVAR(1)
 Sof(N2)=Sof(C17)=FVAR(1)
5.a Riding coordinates:
 O4(H4)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C20(H20), C21(H21)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              682
_olex2_submission_special_instructions 'No special instructions were received'