A Strain Induced Change of Mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 + 1] Cycloaddition Reaction.
Tran-Van, Anne-Florence; Götz, Silas; Neuburger, Markus; Wegner, Hermann A.; Organic letters 16 (2014) 2410–2413; doi:10.1021/ol5007604

data_1515388
_publ_section_title
;
 A Strain Induced Change of Mechanism from a [2 + 2 + 2] to a [2 + 1 + 2 +
 1] Cycloaddition Reaction.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2410
_journal_page_last               2413
_journal_paper_doi               10.1021/ol5007604
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C39.93 H52.38 O6.19'
_chemical_formula_sum            'C39.93 H52.38 O6.19'
_chemical_formula_weight         631.43
_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
_cell_angle_alpha                90.523(6)
_cell_angle_beta                 95.662(6)
_cell_angle_gamma                100.184(6)
_cell_formula_units_Z            2
_cell_length_a                   9.6066(10)
_cell_length_b                   11.7824(13)
_cell_length_c                   15.8331(17)
_cell_measurement_reflns_used    3947
_cell_measurement_temperature    123
_cell_measurement_theta_max      28
_cell_measurement_theta_min      4
_cell_volume                     1754.6(3)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
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_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.757
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             682.959
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.94
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         4417
_refine_ls_number_restraints     1018
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.0079606
_refine_ls_shift/su_mean         0.0003927
_refine_ls_structure_factor_coef F
_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: 
 0.500 0.512 0.213 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1402
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0689
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4417
_reflns_number_total             7930
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0610
_oxford_refine_ls_scale          0.1671(4)
_oxford_reflns_number_all        7910
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            ol5007604_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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.

'_atom_sites_solution_primary' value 'Other' changed to
'other' 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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1515388--1515389.cif.
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_cod_database_code               1515388
_iucr_refine_instruction_details_constraints
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BLOCK SCALE X'S, U'S 
EQUIVALENCE PART(-2002, OCC) 
CONTINUE    PART(-2001, OCC) 
WEIGHT -1   PART(-2001, OCC) 
EQUIVALENCE PART(1001, OCC) 
CONTINUE    PART(1002, OCC) 
WEIGHT -1   PART(1002, OCC) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
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RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) 
RIDE C   (  30,X'S) H   ( 303,X'S) H   ( 302,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) H   ( 353,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 373,X'S) H   ( 372,X'S) H   ( 371,X'S) 
RIDE C   ( 136,X'S) H   (1361,X'S) H   (1362,X'S) 
RIDE C   ( 137,X'S) H   (1371,X'S) H   (1372,X'S) H   (1373,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) H   ( 383,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) H   ( 452,X'S) H   ( 453,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) H   ( 472,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) H   ( 482,X'S) H   ( 483,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) 
REM   SHIFTLIMIT   START (DO NOT REMOVE THIS LINE) 
LIMIT      0.01000000 U[ISO] 
LIMIT      0.01000000 X 
LIMIT      0.01000000 Y 
LIMIT      0.01000000 Z 
LIMIT      0.01000000 U[11] 
LIMIT      0.01000000 U[22] 
LIMIT      0.01000000 U[33] 
LIMIT      0.01000000 U[12] 
LIMIT      0.01000000 U[13] 
LIMIT      0.01000000 U[23] 
LIMIT      0.01000000 OCC 
REM   SHIFTLIMIT   END (DO NOT REMOVE THIS LINE) 
REM   ASSEMBLY1   START (DO NOT REMOVE THIS LINE) 
REM   EXTERNAL BONDS 
DISTANCES  0.0 , 0.01  = MEAN 
CONTINUE C(36) TO C(32) C(136) TO C(32) 
REM   INTERNAL BONDS 
DISTANCES  0.0 , 0.01  = MEAN 
CONTINUE C(36) TO O(6) C(136) TO O(106) 
DISTANCES  0.0 , 0.01  = MEAN 
CONTINUE C(37) TO O(6) C(137) TO O(106) 
REM   ANGLES RESTRAINTS 
ANGLES  0.0 , 0.20  = MEAN 
CONTINUE O(6) TO C(36) TO C(32) O(106) TO C(136) TO C(32) 
ANGLES  0.0 , 0.20  = MEAN 
CONTINUE C(36) TO O(6) TO C(37) C(136) TO O(106) TO C(137) 
REM   VIBRATIONAL RESTRAINTS 
VIBRATIONS 0.0, 0.0100  = 
CONTINUE C(36) TO C(32) C(136) TO C(32) 
CONTINUE C(36) TO O(6) C(136) TO O(106) 
CONTINUE C(37) TO O(6) C(137) TO O(106) 
VIBRATIONS 0.0, 0.00100  = 
CONTINUE C(36) TO C(136) 
CONTINUE C(37) TO C(137) 
CONTINUE O(6) TO O(106) 
REM   SIMILARITY RESTRAINTS 
U(IJ)'S 0.0, 0.00200  = 
CONTINUE C(36) TO C(32) C(136) TO C(32) 
CONTINUE C(36) TO O(6) C(136) TO O(106) 
CONTINUE C(37) TO O(6) C(137) TO O(106) 
U(IJ)'S 0.0, 0.00200  = 
CONTINUE C(36) TO C(136) 
CONTINUE C(37) TO C(137) 
CONTINUE O(6) TO O(106) 
REM   ASSEMBLY1   END (DO NOT REMOVE THIS LINE) 
REM   ASSEMBLY2   START (DO NOT REMOVE THIS LINE) 
REM   GROUP1 
DISTANCES  1.5 , 0.01  = C(38) TO C(39) 
DISTANCES  0.0 , 0.001  = MEAN 
CONTINUE C(39) TO C(40) C(39) TO C(44) C(40) TO C(41) 
CONTINUE C(41) TO C(42) C(42) TO C(43) C(43) TO C(44) 
ANGLES  0.0 , 0.010  = MEAN 
CONTINUE C(38) TO C(39) TO C(40) C(38) TO C(39) TO C(44) 
CONTINUE C(39) TO C(40) TO C(41) C(40) TO C(41) TO C(42) 
CONTINUE C(41) TO C(42) TO C(43) C(42) TO C(43) TO C(44) 
CONTINUE C(43) TO C(44) TO C(39) C(44) TO C(39) TO C(40) 
PLANAR 0.01 FOR C(38) C(39) C(40) C(41) C(42) C(43) C(44) 
VIBRATIONS 0.0, 0.00100  = C(38) TO C(39) 
CONTINUE C(39) TO C(40) C(39) TO C(44) C(40) TO C(41) 
CONTINUE C(41) TO C(42) C(42) TO C(43) C(43) TO C(44) 
U(IJ)'S 0.0, 0.00200  = C(38) TO C(39) 
CONTINUE C(39) TO C(40) C(39) TO C(44) C(40) TO C(41) 
CONTINUE C(41) TO C(42) C(42) TO C(43) C(43) TO C(44) 
REM   GROUP 2 
DISTANCES  1.54 , 0.001  = 
CONTINUE C(45) TO C(46) C(47) TO C(48) 
DISTANCES  1.42 , 0.001  = 
CONTINUE C(46) TO O(7) O(7) TO C(47) 
ANGLES  109.5 , 1.0  = 
CONTINUE C(46) TO O(7) TO C(47) 
CONTINUE C(45) TO C(46) TO O(7) O(7) TO C(47) TO C(48) 
VIBRATIONS 0.0, 0.00100  = 
CONTINUE C(45) TO C(46) C(47) TO C(48) 
CONTINUE C(46) TO O(7) O(7) TO C(47) 
U(IJ)'S 0.0, 0.00200  = 
CONTINUE C(45) TO C(46) C(47) TO C(48) 
CONTINUE C(46) TO O(7) O(7) TO C(47) 
REM   ASSEMBLY2   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;