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_4029193
_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         'C32 H28 N2 O3'
_chemical_formula_sum            'C32 H28 N2 O3'
_chemical_formula_weight         488.56
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-16
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                115.087(3)
_cell_angle_beta                 94.217(3)
_cell_angle_gamma                99.764(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3640(3)
_cell_length_b                   14.8688(7)
_cell_length_c                   15.0929(7)
_cell_measurement_reflns_used    5339
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.317
_cell_measurement_theta_min      3.277
_cell_volume                     1257.67(11)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2011.4-0 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker APEX2 v2011.4-0 (Bruker, 2011)'
_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 0.914
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 APEX'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12899
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         69.200
_diffrn_reflns_theta_min         3.277
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1486 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8147.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       Block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0666P)^2^+0.2336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3410
_reflns_number_total             4230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo4027148_si_004.cif
_cod_data_source_block           baran289
_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               4029193
_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. Restrained distances
 N1-H1
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26),
  C27(H27), C30(H30), C31(H31), C32(H32)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.885
_shelx_hkl_checksum              21883
_shelx_res_checksum              4371
_shelxl_version_number           2013-3