#------------------------------------------------------------------------------
#$Date: 2017-09-12 06:51:39 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/26/4032604.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_4032604
loop_
_publ_author_name
'Lankri, David'
'Albarghouti, Ghassan'
'Mahameed, Mohamed'
'Tsvelikhovsky, Dmitry'
_publ_section_title
;
 Multifaceted α-Enaminone: Adaptable Building Block for Synthesis of
 Heterocyclic Scaffolds Through Conceptually Distinct 1,2-, 1,3-, 1,4-,
 and C-O Bond Forming Annulations.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7101
_journal_page_last               7113
_journal_paper_doi               10.1021/acs.joc.7b00516
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C17 H19 N O'
_chemical_formula_sum            'C17 H19 N O'
_chemical_formula_weight         253.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.082(1)
_cell_length_b                   12.550(2)
_cell_length_c                   13.607(2)
_cell_measurement_reflns_used    8612
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.904
_cell_measurement_theta_min      2.205
_cell_volume                     1380.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15422
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2.05'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0404
_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)+(0.0575P)²+0.2635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                3166
_reflns_number_total             3288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00516_si_003.cif
_cod_data_source_block           davidl4m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032603--4032604.cif.
;
_cod_original_cell_volume        1380.0(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4032604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_refinement_flags
C1 C 0.70473(17) 0.90861(10) 0.60057(10) 0.0255(3) Uani 1 1 d .
H1A H 0.6145 0.8745 0.6384 0.031 Uiso 1 1 calc R
H1B H 0.7300 0.8624 0.5435 0.031 Uiso 1 1 calc R
C2 C 0.64633(19) 1.01659(11) 0.56371(10) 0.0306(3) Uani 1 1 d .
H2A H 0.7346 1.0493 0.5233 0.037 Uiso 1 1 calc R
H2B H 0.6255 1.0639 0.6206 0.037 Uiso 1 1 calc R
C3 C 0.4893(2) 1.00755(15) 0.50270(13) 0.0434(4) Uani 1 1 d .
H3A H 0.3985 0.9823 0.5444 0.065 Uiso 1 1 calc R
H3B H 0.5072 0.9570 0.4488 0.065 Uiso 1 1 calc R
H3C H 0.4610 1.0776 0.4756 0.065 Uiso 1 1 calc R
C4 C 1.00706(17) 0.92310(10) 0.60726(10) 0.0274(3) Uani 1 1 d .
H4A H 1.0899 0.9645 0.6448 0.033 Uiso 1 1 calc R
H4B H 0.9865 0.9605 0.5444 0.033 Uiso 1 1 calc R
C5 C 1.0741(2) 0.81293(12) 0.58662(11) 0.0349(3) Uani 1 1 d .
H5A H 0.9914 0.7712 0.5492 0.042 Uiso 1 1 calc R
H5B H 1.1758 0.8184 0.5463 0.042 Uiso 1 1 calc R
C6 C 0.99076(18) 0.76856(10) 0.74838(11) 0.0281(3) Uani 1 1 d .
C7 C 0.86188(16) 0.84333(9) 0.74259(9) 0.0226(2) Uani 1 1 d .
C8 C 0.74291(16) 0.84444(9) 0.81848(10) 0.0250(3) Uani 1 1 d .
C9 C 0.75222(19) 0.77026(11) 0.89455(10) 0.0308(3) Uani 1 1 d .
H9 H 0.6684 0.7688 0.9435 0.037 Uiso 1 1 calc R
C10 C 0.8828(2) 0.69855(11) 0.89945(11) 0.0353(3) Uani 1 1 d .
H10 H 0.8897 0.6496 0.9526 0.042 Uiso 1 1 calc R
C11 C 1.0022(2) 0.69839(11) 0.82735(12) 0.0345(3) Uani 1 1 d .
H11 H 1.0927 0.6503 0.8315 0.041 Uiso 1 1 calc R
C12 C 0.60885(16) 0.92625(10) 0.82121(9) 0.0250(3) Uani 1 1 d .
C13 C 0.64866(17) 1.03457(10) 0.82405(10) 0.0269(3) Uani 1 1 d .
H13 H 0.7614 1.0560 0.8234 0.032 Uiso 1 1 calc R
C14 C 0.5248(2) 1.11107(12) 0.82778(11) 0.0340(3) Uani 1 1 d .
H14 H 0.5530 1.1845 0.8306 0.041 Uiso 1 1 calc R
C15 C 0.3602(2) 1.08054(13) 0.82735(11) 0.0399(4) Uani 1 1 d .
H15 H 0.2753 1.1329 0.8286 0.048 Uiso 1 1 calc R
C16 C 0.31983(19) 0.97378(14) 0.82515(12) 0.0398(3) Uani 1 1 d .
H16 H 0.2069 0.9528 0.8251 0.048 Uiso 1 1 calc R
C17 C 0.44294(17) 0.89670(12) 0.82300(11) 0.0326(3) Uani 1 1 d .
H17 H 0.4138 0.8234 0.8228 0.039 Uiso 1 1 calc R
N1 N 0.85310(13) 0.91691(8) 0.66342(8) 0.0231(2) Uani 1 1 d .
O1 O 1.11094(13) 0.75983(8) 0.67718(9) 0.0368(3) Uani 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
N1 C1 C2 112.35(10)
N1 C1 H1A 109.1
C2 C1 H1A 109.1
N1 C1 H1B 109.1
C2 C1 H1B 109.1
H1A C1 H1B 107.9
C1 C2 C3 111.88(12)
C1 C2 H2A 109.2
C3 C2 H2A 109.2
C1 C2 H2B 109.2
C3 C2 H2B 109.2
H2A C2 H2B 107.9
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N1 C4 C5 110.72(11)
N1 C4 H4A 109.5
C5 C4 H4A 109.5
N1 C4 H4B 109.5
C5 C4 H4B 109.5
H4A C4 H4B 108.1
O1 C5 C4 109.90(12)
O1 C5 H5A 109.7
C4 C5 H5A 109.7
O1 C5 H5B 109.7
C4 C5 H5B 109.7
H5A C5 H5B 108.2
O1 C6 C11 116.49(12)
O1 C6 C7 122.49(12)
C11 C6 C7 121.02(13)
C6 C7 C8 118.10(12)
C6 C7 N1 120.93(12)
C8 C7 N1 120.96(11)
C9 C8 C7 120.00(12)
C9 C8 C12 118.67(12)
C7 C8 C12 121.30(11)
C10 C9 C8 120.63(13)
C10 C9 H9 119.7
C8 C9 H9 119.7
C11 C10 C9 119.98(13)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C6 120.16(13)
C10 C11 H11 119.9
C6 C11 H11 119.9
C17 C12 C13 118.73(12)
C17 C12 C8 121.09(12)
C13 C12 C8 120.17(12)
C14 C13 C12 120.51(13)
C14 C13 H13 119.7
C12 C13 H13 119.7
C15 C14 C13 120.10(14)
C15 C14 H14 119.9
C13 C14 H14 119.9
C16 C15 C14 119.74(14)
C16 C15 H15 120.1
C14 C15 H15 120.1
C15 C16 C17 120.54(15)
C15 C16 H16 119.7
C17 C16 H16 119.7
C16 C17 C12 120.36(14)
C16 C17 H17 119.8
C12 C17 H17 119.8
C7 N1 C4 112.85(10)
C7 N1 C1 115.72(10)
C4 N1 C1 113.08(10)
C6 O1 C5 114.97(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4764(16)
C1 C2 1.5201(18)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.521(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 N1 1.4622(17)
C4 C5 1.5114(19)
C4 H4A 0.9900
C4 H4B 0.9900
C5 O1 1.4320(19)
C5 H5A 0.9900
C5 H5B 0.9900
C6 O1 1.3762(17)
C6 C11 1.392(2)
C6 C7 1.4041(18)
C7 C8 1.4110(18)
C7 N1 1.4207(15)
C8 C9 1.3943(18)
C8 C12 1.4931(17)
C9 C10 1.388(2)
C9 H9 0.9500
C10 C11 1.376(2)
C10 H10 0.9500
C11 H11 0.9500
C12 C17 1.3913(19)
C12 C13 1.3975(18)
C13 C14 1.3881(19)
C13 H13 0.9500
C14 C15 1.384(2)
C14 H14 0.9500
C15 C16 1.379(3)
C15 H15 0.9500
C16 C17 1.388(2)
C16 H16 0.9500
C17 H17 0.9500
