Paired Utility of Aza-Amino Acyl Proline and Indolizidinone Amino Acid Residues for Peptide Mimicry: Conception of Prostaglandin F2α Receptor Allosteric Modulators That Delay Preterm Birth.
Mir, Fatemeh M.; Atmuri, N. D. Prasad; Bourguet, Carine B.; Fores, Jennifer Rodon; Hou, Xin; Chemtob, Sylvain; Lubell, William D.; Journal of medicinal chemistry 62 (2019) 4500–4525; doi:10.1021/acs.jmedchem.9b00056

data_1552565
_publ_section_title
;
 Paired Utility of Aza-Amino Acyl Proline and Indolizidinone Amino Acid
 Residues for Peptide Mimicry: Conception of Prostaglandin F2\a Receptor
 Allosteric Modulators That Delay Preterm Birth.
;
_journal_issue                   9
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              4500
_journal_page_last               4525
_journal_paper_doi               10.1021/acs.jmedchem.9b00056
_journal_volume                  62
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H26 N2 O4'
_chemical_formula_sum            'C24 H26 N2 O4'
_chemical_formula_weight         406.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 116.589(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4081(12)
_cell_length_b                   16.2769(16)
_cell_length_c                   12.6451(18)
_cell_measurement_reflns_used    9703
_cell_measurement_temperature    150
_cell_measurement_theta_max      53.995
_cell_measurement_theta_min      3.401
_cell_volume                     2099.7(4)
_computing_cell_refinement
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27430
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.109
_diffrn_reflns_theta_min         2.362
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.4730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1418 before and 0.0961 after correction. The Ratio of minimum to maximum transmission is 0.6302. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.325
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.571
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.571
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.1453
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3377
_refine_ls_wR_factor_ref         0.3547
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                6616
_reflns_number_total             7671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm9b00056_si_003.cif
_cod_data_source_block           lub1032
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1552565
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5(9)
 -0.11(12) 0.3(9) 0.30(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C2B(H2BA), C5B(H5B), C8B(H8B), C2A(H2AA), C5A(H5A), C8A(H8A)
3.b Secondary CH2 refined with riding coordinates:
 C3B(H3BA,H3BB), C4B(H4BA,H4BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C10B(H10C,
 H10D), C18B(H18C,H18D), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C6A(H6AA,H6AB),
 C7A(H7AA,H7AB), C10A(H10A,H10B), C18A(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 N2B(H2B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B),
 C20B(H20B), C21B(H21B), C22B(H22B), C23B(H23B), C24B(H24B), N2A(H2A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A), C20A(H20A),
 C21A(H21A), C22A(H22A), C24A(H24A), C23A(H23A)
;
_shelx_res_checksum              73627
_shelx_hkl_checksum              61654
_olex2_exptl_crystal_mounting_method 'mounted on a Mylar Cryoloop'
_olex2_submission_original_sample_id WDL-PRA-27
_olex2_submission_special_instructions 'No special instructions were received'