Applications of C-h functionalization logic to cyclobutane synthesis.
Gutekunst, Will R.; Baran, Phil S.; The Journal of organic chemistry 79 (2014) 2430–2452; doi:10.1021/jo4027148

data_4029191
_publ_section_title
;
 Applications of C-h functionalization logic to cyclobutane synthesis.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2430
_journal_page_last               2452
_journal_paper_doi               10.1021/jo4027148
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C44 H36 N4 O5 S2, C H2 Cl2'
_chemical_formula_sum            'C45 H38 Cl2 N4 O5 S2'
_chemical_formula_weight         849.81
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                110.732(14)
_cell_angle_beta                 108.300(10)
_cell_angle_gamma                100.249(10)
_cell_formula_units_Z            2
_cell_length_a                   9.969(8)
_cell_length_b                   15.383(12)
_cell_length_c                   15.774(15)
_cell_measurement_reflns_used    9809
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.937
_cell_measurement_theta_min      2.281
_cell_volume                     2031(3)
_computing_cell_refinement       'SAINT v7.56A (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.56A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device       'Siemens P4 Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker P4 APEX Mo'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28205
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.152
_diffrn_reflns_theta_min         1.497
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0946 before and 0.0692 after correction.
The Ratio of minimum to maximum transmission is 0.8089.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       Plate
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.105
_platon_squeeze_details
;
 SQUEEZE found one void was found containing 2 disordered molecules of  dichloromethane. 
 Their formula was added to the formula for the unit-cell and the  electron density removed.
;
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1031P)^2^+0.7912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1711
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7111
_reflns_number_total             8867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo4027148_si_005.cif
_cod_data_source_block           Baran102
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/current/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4029191
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C18(H18), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C32(H32),
  C33(H33), C34(H34), C35(H35), C37(H37), C39(H39), C40(H40), C42(H42), C43(H43)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              78423
_shelx_hkl_checksum              42440