Synthesis and late-stage C-H functionalization of papaverines.
Suresh, Sundararajan; Nawaz Khan, Fazlur Rahman; Organic & biomolecular chemistry 23 (2025) 8431–8436; doi:10.1039/d5ob01155h

data_7160779
_publ_section_title
;
 Synthesis and late-stage C-H functionalization of papaverines.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8431
_journal_page_last               8436
_journal_paper_doi               10.1039/d5ob01155h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C27 H24 Cl N O4'
_chemical_formula_sum            'C27 H24 Cl N O4'
_chemical_formula_weight         461.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-29 deposited with the CCDC.	2025-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.402(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0817(18)
_cell_length_b                   21.482(3)
_cell_length_c                   8.3972(13)
_cell_measurement_reflns_used    6709
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      22.05
_cell_measurement_theta_min      2.46
_cell_volume                     2349.3(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            45351
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_min         1.896
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.171
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0665
_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^)+(0.1082P)^2^+0.8789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.2505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2378
_reflns_number_total             5599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01155h2.cif
_cod_data_source_block           b_1_190624_0m_a
_cod_database_code               7160779
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
O1: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 within
2A
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C21(H21), C24(H24), C25(H25)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              78043
_olex2_submission_special_instructions 'No special instructions were received'