A Design of Experiments Approach to a Robust Final Deprotection and Reactive Crystallization of IPI-926, A Novel Hedgehog Pathway Inhibitor
Martinot, Theodore A.; Austad, Brian C.; Côté, Alexandre; Depew, Kristopher M.; Genov, Daniel; Grenier, Louis; Helble, Joseph; Lescarbeau, Andre; Nair, Somarajan; Trudeau, Martin; White, Priscilla; Yu, Lin-Chen; Organic Process Research & Development 19 (2015) 1693–; doi:10.1021/acs.oprd.5b00214

data_1530688
_publ_section_title
;
 A Design of Experiments Approach to a Robust Final Deprotection and
 Reactive Crystallization of IPI-926, A Novel Hedgehog Pathway Inhibitor
;
_journal_issue                   11
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              1693
_journal_paper_doi               10.1021/acs.oprd.5b00214
_journal_volume                  19
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H53 N3 O4 S1'
_chemical_formula_sum            'C36 H53 N3 O4 S'
_chemical_formula_weight         623.91
_space_group_IT_number           3
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2y'
_symmetry_space_group_name_H-M   'P 1 2 1'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 112.422(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.4743(12)
_cell_length_b                   8.7109(6)
_cell_length_c                   22.4995(14)
_cell_measurement_reflns_used    49808
_cell_measurement_temperature    150.00(2)
_cell_measurement_theta_max      66
_cell_measurement_theta_min      7
_cell_volume                     3709.4(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution
;
 Direct methods (SIR2004, Burla et al., 2005)
;
_diffrn_ambient_temperature      150.00(2)
_diffrn_measured_fraction_theta_full 0.9910
_diffrn_measured_fraction_theta_max 0.9910
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           CU-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_av_sigmaI/netI    0.1423
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            49808
_diffrn_reflns_theta_full        60.0
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_min         6.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.7920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_platon_squeeze_details
'                                                                       '
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.55
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_d_res_high            0.89
_refine_ls_extinction_coef       0.26E-02
_refine_ls_extinction_method     'SHELXL97 (Sheldrick 2008)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     798
_refine_ls_number_reflns         10790
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.161
_refine_ls_R_factor_gt           0.099
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.1650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.235
_refine_ls_wR_factor_ref         0.285
_reflns_Friedel_coverage         1.0000
_reflns_number_gt                5687
_reflns_number_total             10790
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            op5b00214_si_004.cif
_cod_data_source_block           224792
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1530688--1530690.cif.

The following automatic conversions were performed:

data name '_exptl_absorpt__process_details' was replaced with
'_exptl_absorpt_process_details' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_formula_sum        'C36 H53 N3 O4 S1'
_cod_database_code               1530688