#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:23:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180180 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/76/7107670.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_7107670
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         'C19 H23 N O4'
_chemical_formula_sum            'C19 H23 N O4'
_chemical_formula_weight         329.38
_chemical_melting_point          411
_chemical_name_systematic
;
1,1'-(1-Benzyl-4-(dimethoxymethyl)-1,4-dihydropyridine-3,5-diyl)diethanone
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-02-03
_audit_creation_method
;
Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0102(2)
_cell_length_b                   13.7886(3)
_cell_length_c                   20.7109(4)
_cell_measurement_reflns_used    8110
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.403
_cell_measurement_theta_min      2.597
_cell_volume                     3429.80(11)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_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  0.0460
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30328
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.97
_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    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0355
_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)+(0.0496P)²+0.8379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                2384
_reflns_number_total             3028
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2cc31495a.txt
_cod_data_source_block           4e
_cod_database_code               7107670
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'
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
_atom_site_refinement_flags
O1 O -0.02868(9) 0.43867(8) 0.39203(7) 0.0442(3) Uani 1 1 d .
O2 O 0.03596(9) 0.72338(8) 0.25786(5) 0.0321(3) Uani 1 1 d .
O3 O 0.08861(8) 0.73604(7) 0.40478(5) 0.0271(2) Uani 1 1 d .
O4 O 0.22472(8) 0.63176(7) 0.43586(5) 0.0254(2) Uani 1 1 d .
N1 N 0.32814(9) 0.51143(9) 0.31102(6) 0.0250(3) Uani 1 1 d .
C1 C 0.44232(12) 0.47974(11) 0.29905(7) 0.0282(3) Uani 1 1 d .
H1A H 0.4661 0.5047 0.2564 0.034 Uiso 1 1 calc R
H1B H 0.4434 0.4080 0.2968 0.034 Uiso 1 1 calc R
C2 C 0.25349(12) 0.45058(10) 0.34098(6) 0.0237(3) Uani 1 1 d .
H2 H 0.2767 0.3868 0.3520 0.028 Uiso 1 1 calc R
C3 C 0.14863(11) 0.47808(10) 0.35528(6) 0.0223(3) Uani 1 1 d .
C4 C 0.11381(11) 0.58266(10) 0.34687(7) 0.0226(3) Uani 1 1 d .
H4 H 0.0352 0.5833 0.3310 0.027 Uiso 1 1 calc R
C5 C 0.18573(12) 0.63063(10) 0.29628(7) 0.0232(3) Uani 1 1 d .
C6 C 0.28936(12) 0.59706(10) 0.28506(7) 0.0244(3) Uani 1 1 d .
H6 H 0.3376 0.6339 0.2582 0.029 Uiso 1 1 calc R
C7 C 0.06544(12) 0.40967(11) 0.37994(7) 0.0272(3) Uani 1 1 d .
C8 C 0.09251(13) 0.30427(11) 0.38848(8) 0.0335(4) Uani 1 1 d .
H8A H 0.0449 0.2767 0.4223 0.050 Uiso 1 1 calc R
H8B H 0.1708 0.2974 0.4010 0.050 Uiso 1 1 calc R
H8C H 0.0795 0.2698 0.3478 0.050 Uiso 1 1 calc R
C9 C 0.13663(13) 0.70654(10) 0.25553(7) 0.0264(3) Uani 1 1 d .
C10 C 0.20836(14) 0.76123(12) 0.20809(8) 0.0356(4) Uani 1 1 d .
H10A H 0.2221 0.7206 0.1701 0.053 Uiso 1 1 calc R
H10B H 0.2795 0.7778 0.2285 0.053 Uiso 1 1 calc R
H10C H 0.1701 0.8208 0.1949 0.053 Uiso 1 1 calc R
C11 C 0.52577(12) 0.51203(10) 0.34915(7) 0.0247(3) Uani 1 1 d .
C12 C 0.63802(12) 0.49206(11) 0.33800(8) 0.0293(3) Uani 1 1 d .
H12 H 0.6595 0.4599 0.2994 0.035 Uiso 1 1 calc R
C13 C 0.71812(13) 0.51837(12) 0.38235(8) 0.0364(4) Uani 1 1 d .
H13 H 0.7944 0.5048 0.3741 0.044 Uiso 1 1 calc R
C14 C 0.68723(14) 0.56469(12) 0.43905(9) 0.0382(4) Uani 1 1 d .
H14 H 0.7421 0.5824 0.4699 0.046 Uiso 1 1 calc R
C15 C 0.57674(14) 0.58489(12) 0.45040(8) 0.0357(4) Uani 1 1 d .
H15 H 0.5557 0.6169 0.4891 0.043 Uiso 1 1 calc R
C16 C 0.49574(13) 0.55887(11) 0.40576(8) 0.0293(4) Uani 1 1 d .
H16 H 0.4197 0.5732 0.4140 0.035 Uiso 1 1 calc R
C17 C 0.11704(12) 0.63639(10) 0.41178(7) 0.0227(3) Uani 1 1 d .
H17 H 0.0646 0.6047 0.4428 0.027 Uiso 1 1 calc R
C18 C -0.02830(13) 0.75156(12) 0.40540(8) 0.0361(4) Uani 1 1 d .
H18A H -0.0616 0.7218 0.3670 0.054 Uiso 1 1 calc R
H18B H -0.0436 0.8214 0.4053 0.054 Uiso 1 1 calc R
H18C H -0.0603 0.7222 0.4443 0.054 Uiso 1 1 calc R
C19 C 0.23240(13) 0.66445(12) 0.50133(7) 0.0322(4) Uani 1 1 d .
H19A H 0.2228 0.7350 0.5027 0.048 Uiso 1 1 calc R
H19B H 0.3056 0.6474 0.5189 0.048 Uiso 1 1 calc R
H19C H 0.1741 0.6334 0.5272 0.048 Uiso 1 1 calc R
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
C18 O3 C17 112.44(11)
C17 O4 C19 112.70(11)
C2 N1 C1 120.40(12)
C2 N1 C6 118.56(12)
C6 N1 C1 120.48(12)
N1 C1 C11 114.73(12)
C3 C2 N1 122.43(13)
C2 C3 C4 120.10(13)
C2 C3 C7 122.16(13)
C7 C3 C4 117.74(12)
C3 C4 C17 110.64(11)
C5 C4 C3 109.84(11)
C5 C4 C17 112.43(11)
C6 C5 C4 119.82(13)
C6 C5 C9 121.10(13)
C9 C5 C4 118.77(12)
C5 C6 N1 122.60(13)
O1 C7 C3 119.35(13)
O1 C7 C8 119.49(14)
C3 C7 C8 121.12(13)
O2 C9 C5 120.40(13)
O2 C9 C10 119.45(13)
C5 C9 C10 120.09(13)
C12 C11 C1 118.00(13)
C16 C11 C1 123.09(13)
C16 C11 C12 118.90(14)
C13 C12 C11 120.80(15)
C12 C13 C14 119.90(15)
C15 C14 C13 119.72(15)
C14 C15 C16 120.61(16)
C11 C16 C15 120.07(14)
O3 C17 C4 111.75(11)
O4 C17 O3 107.74(11)
O4 C17 C4 108.42(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2249(18)
O2 C9 1.2320(18)
O3 C17 1.4232(16)
O3 C18 1.4204(18)
O4 C17 1.3876(17)
O4 C19 1.4318(17)
N1 C1 1.4605(18)
N1 C2 1.3758(18)
N1 C6 1.3785(19)
C1 C11 1.510(2)
C2 C3 1.348(2)
C3 C4 1.512(2)
C3 C7 1.466(2)
C4 C5 1.510(2)
C4 C17 1.5354(19)
C5 C6 1.348(2)
C5 C9 1.468(2)
C7 C8 1.500(2)
C9 C10 1.509(2)
C11 C12 1.395(2)
C11 C16 1.386(2)
C12 C13 1.379(2)
C13 C14 1.387(2)
C14 C15 1.376(2)
C15 C16 1.389(2)
