#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:23:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180180 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/76/7107672.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7107672
loop_
_publ_author_name
'P. Ricardo Girling'
'Andrei Batsanov'
'Hong Shen'
'Andrew Whiting'
_publ_section_title
;
 A multicomponent formal [1+2+2+1]-cycloaddition for the Synthesis of
 dihydropyridines
;
_journal_name_full               Chem.Commun.
_journal_page_first              4893
_journal_page_last               4895
_journal_paper_doi               10.1039/c2cc31495a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C18 H18 N2 O4'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34
_chemical_melting_point          379.7(5)
_chemical_name_systematic
;
1,1'-(1-Allyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-diyl)diethanone
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-12
_audit_creation_method
;
Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                95.465(2)
_cell_angle_beta                 99.984(2)
_cell_angle_gamma                93.148(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0656(3)
_cell_length_b                   8.3174(3)
_cell_length_c                   12.3033(4)
_cell_measurement_reflns_used    4742
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.90
_cell_measurement_theta_min      2.49
_cell_volume                     807.02(5)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13943
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         1.69
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.6693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0375 before and 0.0259 after correction.
The Ratio of minimum to maximum transmission is 0.7763.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.3P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1349
_reflns_number_gt                3510
_reflns_number_total             4499
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c2cc31495a.txt
_cod_data_source_block           4g
_cod_database_code               7107672
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.06037(12) -0.09224(11) 0.60772(8) 0.0265(2) Uani 1 1 d
O2 O -0.34875(11) 0.34815(11) 0.58650(8) 0.0290(2) Uani 1 1 d
O3 O -0.34588(17) -0.07884(18) 1.05590(11) 0.0524(3) Uani 1 1 d
O4 O -0.20248(19) 0.13255(17) 1.14893(10) 0.0543(4) Uani 1 1 d
N1 N 0.23821(13) 0.46256(12) 0.70538(9) 0.0240(2) Uani 1 1 d
N2 N -0.25259(17) 0.04435(17) 1.06261(11) 0.0376(3) Uani 1 1 d
C1 C 0.26659(15) 0.30036(15) 0.68803(10) 0.0225(2) Uani 1 1 d
C2 C 0.14081(15) 0.18298(14) 0.66142(10) 0.0208(2) Uani 1 1 d
C3 C -0.04059(15) 0.22093(14) 0.66360(10) 0.0202(2) Uani 1 1 d
C4 C -0.05775(15) 0.39859(14) 0.64850(10) 0.0213(2) Uani 1 1 d
C5 C 0.07707(15) 0.50782(15) 0.67385(10) 0.0224(2) Uani 1 1 d
C6 C 0.38431(16) 0.58186(16) 0.73179(12) 0.0258(3) Uani 1 1 d
C7 C 0.47412(18) 0.58427(17) 0.84924(12) 0.0309(3) Uani 1 1 d
C8 C 0.6297(2) 0.5431(2) 0.87704(15) 0.0452(4) Uani 1 1 d
C9 C 0.17468(16) 0.01544(14) 0.62757(10) 0.0219(2) Uani 1 1 d
C10 C 0.35272(18) -0.02092(17) 0.61621(13) 0.0291(3) Uani 1 1 d
C11 C -0.22645(15) 0.44849(15) 0.60599(10) 0.0225(2) Uani 1 1 d
C12 C -0.24958(17) 0.62349(17) 0.58777(13) 0.0282(3) Uani 1 1 d
C13 C -0.09562(15) 0.17548(14) 0.76986(10) 0.0213(2) Uani 1 1 d
C14 C -0.21383(17) 0.04621(17) 0.76554(11) 0.0277(3) Uani 1 1 d
C15 C -0.26585(18) 0.00199(18) 0.86122(12) 0.0321(3) Uani 1 1 d
C16 C -0.19724(17) 0.09045(17) 0.96100(11) 0.0285(3) Uani 1 1 d
C17 C -0.0785(2) 0.21852(18) 0.96926(12) 0.0323(3) Uani 1 1 d
C18 C -0.02788(19) 0.26044(17) 0.87248(11) 0.0301(3) Uani 1 1 d
H1 H 0.383(2) 0.2811(19) 0.6930(13) 0.025(4) Uiso 1 1 d
H3 H -0.116(2) 0.1524(19) 0.6007(13) 0.024(4) Uiso 1 1 d
H5 H 0.0699(19) 0.6216(19) 0.6699(13) 0.024(4) Uiso 1 1 d
H6A H 0.339(2) 0.686(2) 0.7181(15) 0.035(4) Uiso 1 1 d
H6B H 0.462(2) 0.552(2) 0.6779(15) 0.036(4) Uiso 1 1 d
H7 H 0.410(2) 0.622(2) 0.9051(16) 0.038(5) Uiso 1 1 d
H8A H 0.682(3) 0.551(2) 0.9556(17) 0.048(5) Uiso 1 1 d
H8B H 0.697(3) 0.504(3) 0.821(2) 0.061(6) Uiso 1 1 d
H10A H 0.351(2) -0.131(2) 0.5765(15) 0.037(5) Uiso 1 1 d
H10B H 0.422(3) -0.015(2) 0.6886(18) 0.048(5) Uiso 1 1 d
H10C H 0.401(2) 0.058(2) 0.5751(16) 0.043(5) Uiso 1 1 d
H12A H -0.233(2) 0.691(2) 0.6585(18) 0.048(5) Uiso 1 1 d
H12B H -0.365(2) 0.633(2) 0.5473(15) 0.034(4) Uiso 1 1 d
H12C H -0.164(2) 0.667(2) 0.5471(16) 0.045(5) Uiso 1 1 d
H14 H -0.259(2) -0.015(2) 0.6927(14) 0.030(4) Uiso 1 1 d
H15 H -0.351(2) -0.088(2) 0.8563(16) 0.040(5) Uiso 1 1 d
H17 H -0.033(2) 0.279(2) 1.0396(16) 0.040(5) Uiso 1 1 d
H18 H 0.059(2) 0.351(2) 0.8772(15) 0.039(5) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C6 118.55(10)
C5 N1 C1 118.20(10)
C5 N1 C6 121.70(10)
O3 N2 C16 118.44(13)
O4 N2 O3 123.90(13)
O4 N2 C16 117.66(14)
N1 C1 H1 113.5(9)
C2 C1 N1 122.75(11)
C2 C1 H1 123.6(9)
C1 C2 C3 120.69(11)
C1 C2 C9 120.99(11)
C9 C2 C3 118.32(10)
C2 C3 C13 111.22(9)
C2 C3 H3 108.4(9)
C4 C3 C2 108.75(9)
C4 C3 C13 112.36(10)
C4 C3 H3 109.6(9)
C13 C3 H3 106.4(9)
C5 C4 C3 121.38(11)
C5 C4 C11 120.88(11)
C11 C4 C3 117.75(10)
N1 C5 H5 114.3(9)
C4 C5 N1 122.02(11)
C4 C5 H5 123.7(9)
N1 C6 C7 112.14(11)
N1 C6 H6A 105.3(10)
N1 C6 H6B 106.7(10)
C7 C6 H6A 111.3(10)
C7 C6 H6B 110.8(10)
H6A C6 H6B 110.2(14)
C6 C7 H7 115.1(11)
C8 C7 C6 123.87(15)
C8 C7 H7 121.0(11)
C7 C8 H8A 119.7(12)
C7 C8 H8B 122.2(13)
H8A C8 H8B 118.1(18)
O1 C9 C2 120.63(11)
O1 C9 C10 120.67(11)
C2 C9 C10 118.69(11)
C9 C10 H10A 108.9(10)
C9 C10 H10B 109.5(12)
C9 C10 H10C 110.4(11)
H10A C10 H10B 110.3(16)
H10A C10 H10C 109.8(15)
H10B C10 H10C 107.8(16)
O2 C11 C4 119.98(11)
O2 C11 C12 120.27(11)
C4 C11 C12 119.74(11)
C11 C12 H12A 110.6(12)
C11 C12 H12B 109.5(10)
C11 C12 H12C 111.4(11)
H12A C12 H12B 108.8(15)
H12A C12 H12C 105.8(16)
H12B C12 H12C 110.7(15)
C14 C13 C3 119.99(11)
C14 C13 C18 118.82(12)
C18 C13 C3 121.19(11)
C13 C14 C15 121.14(13)
C13 C14 H14 118.3(10)
C15 C14 H14 120.5(10)
C14 C15 H15 119.9(11)
C16 C15 C14 118.23(13)
C16 C15 H15 121.8(11)
C15 C16 N2 118.40(13)
C17 C16 N2 119.03(13)
C17 C16 C15 122.56(12)
C16 C17 C18 118.25(13)
C16 C17 H17 121.2(11)
C18 C17 H17 120.6(11)
C13 C18 H18 119.8(11)
C17 C18 C13 120.99(13)
C17 C18 H18 119.2(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.2253(15)
O2 C11 1.2314(15)
O3 N2 1.2250(19)
O4 N2 1.2246(19)
N1 C1 1.3835(16)
N1 C5 1.3741(16)
N1 C6 1.4684(16)
N2 C16 1.4748(17)
C1 C2 1.3434(17)
C1 H1 0.951(16)
C2 C3 1.5178(16)
C2 C9 1.4699(17)
C3 C4 1.5176(16)
C3 C13 1.5251(16)
C3 H3 1.003(16)
C4 C5 1.3509(17)
C4 C11 1.4676(17)
C5 H5 0.957(16)
C6 C7 1.498(2)
C6 H6A 0.978(18)
C6 H6B 1.012(18)
C7 C8 1.315(2)
C7 H7 0.967(19)
C8 H8A 0.98(2)
C8 H8B 1.00(2)
C9 C10 1.5107(18)
C10 H10A 0.996(18)
C10 H10B 0.96(2)
C10 H10C 0.97(2)
C11 C12 1.5103(18)
C12 H12A 0.97(2)
C12 H12B 0.985(18)
C12 H12C 0.99(2)
C13 C14 1.3881(17)
C13 C18 1.3930(18)
C14 C15 1.3906(19)
C14 H14 0.988(17)
C15 C16 1.379(2)
C15 H15 0.980(19)
C16 C17 1.377(2)
C17 C18 1.392(2)
C17 H17 0.961(19)
C18 H18 0.988(18)
