De novo synthesis of multisubstituted aryl amines using alkene cross metathesis.
Tatton, Matthew R; Simpson, Iain; Donohoe, Timothy J; Organic letters 16 (2014) 1920–1923; doi:10.1021/ol500441q

data_1514216
_publ_section_title
;
 De novo synthesis of multisubstituted aryl amines using alkene cross
 metathesis.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1920
_journal_page_last               1923
_journal_paper_doi               10.1021/ol500441q
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C26 H21 N1 O2 S1'
_chemical_formula_sum            'C26 H21 N O2 S'
_chemical_formula_weight         411.52
_chemical_melting_point          ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             14-01-28
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                87.937(3)
_cell_angle_beta                 97.022(3)
_cell_angle_gamma                88.976(3)
_cell_formula_units_Z            4
_cell_length_a                   13.2870(5)
_cell_length_b                   11.2749(3)
_cell_length_c                   13.4828(5)
_cell_measurement_reflns_used    7497
_cell_measurement_temperature    120
_cell_measurement_theta_max      30
_cell_measurement_theta_min      4
_cell_volume                     2002.90(12)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution
'Expansion and refinement the structure at 300 K'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10166
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         30.049
_diffrn_reflns_theta_min         1.808
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9729
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         10133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.0004984
_refine_ls_shift/su_mean         0.0000177
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.113E+04 0.171E+04 990. 361. 47.4 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1336
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1336
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                7728
_reflns_number_total             10166
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.53
_oxford_diffrn_Wilson_scale      0.09
_oxford_refine_ls_r_factor_ref   0.0778
_oxford_refine_ls_scale          3.96(4)
_oxford_reflns_number_all        10133
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 043tjd14-120K
_cod_data_source_file            ol500441q_si_002.cif
_cod_data_source_block           7-120K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary'
value 'Other' changed to 'other' according to
/usr/data/users/saulius/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514216.cif.
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C26 H21 N1 O2 S1'
_cod_database_code               1514216
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 402,X'S) H   ( 403,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;