Synthesis and Diels-Alder Reactivity of Substituted [4]Dendralenes.
Saglam, Mehmet F.; Alborzi, Ali R.; Payne, Alan D.; Willis, Anthony C.; Paddon-Row, Michael N; Sherburn, Michael S.; The Journal of organic chemistry 81 (2016) 1461–1475; doi:10.1021/acs.joc.5b02583

data_4031879
_publ_section_title
;
 Synthesis and Diels-Alder Reactivity of Substituted [4]Dendralenes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1461
_journal_page_last               1475
_journal_paper_doi               10.1021/acs.joc.5b02583
_journal_volume                  81
_journal_year                    2016
_chemical_compound_source        local
_chemical_formula_moiety         'C19 H22 N2 O4'
_chemical_formula_sum            'C19 H22 N2 O4'
_chemical_formula_weight         342.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-02-10
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-02-14 - Report on C19 H22 N2 O4
             by Anthony C. Willis
             for Mehmet Saglam and Mick Sherburn
2012-02-14 - passes checkcif tests with minor warnings
2015-08-26 - CCDC version
;
_cell_angle_alpha                90
_cell_angle_beta                 99.532(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5131(4)
_cell_length_b                   15.5780(10)
_cell_length_c                   17.3470(11)
_cell_measurement_reflns_used    203835
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1735.74(19)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.045
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26224
_diffrn_reflns_theta_full        27.490
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.615
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0481
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3970
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.0076129
_refine_ls_shift/su_mean         0.0012389
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.11P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1554
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1554
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2851
_reflns_number_total             3970
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.59
_oxford_diffrn_Wilson_scale      1.22
_oxford_refine_ls_r_factor_ref   0.0897
_oxford_refine_ls_scale          0.962(5)
_oxford_reflns_number_all        3970
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '2101111 she1202'
_cod_data_source_file            jo5b02583_si_001.cif
_cod_data_source_block           compound_47
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1735.75(19)
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4031879
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, C(1,U'S) UNTIL O(25) 
CONT C(71,U[ISO],OCC) C(19,OCC) 
EQUIV C(19,OCC) C(71,OCC) 
WEIGHT -1 C(71,OCC) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) H   ( 712,X'S) H   ( 713,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 1.49, .02 = C(7) TO C(71) 
ANGLE 116, 2. = C(8) TO C(7) TO C(71) 
ANGLE 126, 2. = C(6) TO C(7) TO C(71) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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