#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:31:12 +0100 (lun 21 de mar de 2016) $
#$Revision: 178482 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/03/4030373.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_4030373
loop_
_publ_author_name
'Zhu, Yuequan'
'Gong, Yuefa'
_publ_section_title
;
 Construction of 2-Pyrone Skeleton via Domino Sequence between
 2-Acyl-1-Chlorocyclopropanecarboxylate and Amines.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              490
_journal_paper_doi               10.1021/jo502502z
_journal_volume                  80
_journal_year                    2014
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 107.601(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7708(19)
_cell_length_b                   16.326(3)
_cell_length_c                   7.5417(13)
_cell_measurement_reflns_used    5454
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.07
_cell_measurement_theta_min      2.34
_cell_volume                     1264.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11901
_diffrn_reflns_theta_full        30.99
_diffrn_reflns_theta_max         30.99
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0399
_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)+(0.0674P)²+0.2955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                3408
_reflns_number_total             3972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502502z_si_002.cif
_cod_data_source_block           g:\140618e\work\t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--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 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030373.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4030373
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
C1 C -0.38528(10) 0.11908(6) -0.36973(13) 0.02092(19) Uani 1 1 d .
H1A H -0.3883 0.1734 -0.4262 0.031 Uiso 1 1 calc R
H1B H -0.4729 0.1035 -0.3687 0.031 Uiso 1 1 calc R
H1C H -0.3532 0.0790 -0.4421 0.031 Uiso 1 1 calc R
C2 C -0.29525(9) 0.12123(5) -0.17321(13) 0.01648(17) Uani 1 1 d .
C3 C -0.17305(9) 0.08454(6) -0.12656(13) 0.01821(18) Uani 1 1 d .
H3 H -0.1459 0.0577 -0.2203 0.022 Uiso 1 1 calc R
C4 C -0.08973(9) 0.08648(6) 0.05542(13) 0.01753(18) Uani 1 1 d .
H4 H -0.0064 0.0614 0.0835 0.021 Uiso 1 1 calc R
C5 C -0.12718(9) 0.12485(5) 0.19729(12) 0.01513(17) Uani 1 1 d .
C6 C -0.25095(9) 0.16128(5) 0.15077(13) 0.01715(18) Uani 1 1 d .
H6 H -0.2791 0.1872 0.2446 0.021 Uiso 1 1 calc R
C7 C -0.33232(9) 0.15974(5) -0.03094(13) 0.01752(18) Uani 1 1 d .
H7 H -0.4152 0.1854 -0.0598 0.021 Uiso 1 1 calc R
C8 C -0.03844(9) 0.12953(5) 0.38696(13) 0.01538(17) Uani 1 1 d .
C9 C 0.17650(9) 0.08389(6) 0.57324(13) 0.01731(18) Uani 1 1 d .
C10 C 0.16086(9) 0.13188(5) 0.72981(12) 0.01539(17) Uani 1 1 d .
C11 C 0.04832(9) 0.17608(6) 0.70300(13) 0.01792(18) Uani 1 1 d .
H11 H 0.0368 0.2077 0.8026 0.022 Uiso 1 1 calc R
C12 C -0.05117(9) 0.17546(6) 0.52962(13) 0.01818(18) Uani 1 1 d .
H12 H -0.1274 0.2076 0.5136 0.022 Uiso 1 1 calc R
C13 C 0.35836(9) 0.06872(6) 0.96015(13) 0.01756(18) Uani 1 1 d .
H13A H 0.4302 0.0706 0.9037 0.021 Uiso 1 1 calc R
H13B H 0.3150 0.0147 0.9341 0.021 Uiso 1 1 calc R
C14 C 0.40896(10) 0.08490(6) 1.16972(14) 0.0223(2) Uani 1 1 d .
H14A H 0.3604 0.0520 1.2370 0.027 Uiso 1 1 calc R
H14B H 0.5028 0.0716 1.2194 0.027 Uiso 1 1 calc R
C15 C 0.38547(10) 0.17657(6) 1.18790(13) 0.02026(19) Uani 1 1 d .
H15A H 0.3799 0.1901 1.3132 0.024 Uiso 1 1 calc R
H15B H 0.4552 0.2098 1.1628 0.024 Uiso 1 1 calc R
C16 C 0.25585(9) 0.18972(6) 1.03969(13) 0.01911(18) Uani 1 1 d .
H16A H 0.1823 0.1739 1.0857 0.023 Uiso 1 1 calc R
H16B H 0.2450 0.2476 0.9988 0.023 Uiso 1 1 calc R
N1 N 0.26432(8) 0.13586(5) 0.88851(11) 0.01759(16) Uani 1 1 d .
O1 O 0.07266(7) 0.08343(4) 0.41246(9) 0.01815(15) Uani 1 1 d .
O2 O 0.27200(7) 0.04579(5) 0.57014(11) 0.02720(18) 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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C7 117.79(8)
C3 C2 C1 121.14(8)
C7 C2 C1 121.06(8)
C2 C3 C4 121.14(8)
C2 C3 H3 119.4
C4 C3 H3 119.4
C3 C4 C5 120.92(8)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C6 118.01(8)
C4 C5 C8 121.11(8)
C6 C5 C8 120.84(8)
C7 C6 C5 120.55(8)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C2 121.58(8)
C6 C7 H7 119.2
C2 C7 H7 119.2
C12 C8 O1 119.01(8)
C12 C8 C5 127.86(8)
O1 C8 C5 113.04(7)
O2 C9 O1 116.69(8)
O2 C9 C10 126.54(9)
O1 C9 C10 116.76(8)
N1 C10 C11 123.60(8)
N1 C10 C9 117.88(8)
C11 C10 C9 118.23(8)
C10 C11 C12 121.32(8)
C10 C11 H11 119.3
C12 C11 H11 119.3
C8 C12 C11 120.50(8)
C8 C12 H12 119.7
C11 C12 H12 119.7
N1 C13 C14 103.88(7)
N1 C13 H13A 111.0
C14 C13 H13A 111.0
N1 C13 H13B 111.0
C14 C13 H13B 111.0
H13A C13 H13B 109.0
C15 C14 C13 104.14(8)
C15 C14 H14A 110.9
C13 C14 H14A 110.9
C15 C14 H14B 110.9
C13 C14 H14B 110.9
H14A C14 H14B 108.9
C16 C15 C14 102.27(7)
C16 C15 H15A 111.3
C14 C15 H15A 111.3
C16 C15 H15B 111.3
C14 C15 H15B 111.3
H15A C15 H15B 109.2
N1 C16 C15 103.22(7)
N1 C16 H16A 111.1
C15 C16 H16A 111.1
N1 C16 H16B 111.1
C15 C16 H16B 111.1
H16A C16 H16B 109.1
C10 N1 C16 118.92(7)
C10 N1 C13 124.81(7)
C16 N1 C13 110.95(7)
C8 O1 C9 124.01(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5063(13)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.3911(13)
C2 C7 1.4018(13)
C3 C4 1.3947(13)
C3 H3 0.9500
C4 C5 1.4003(12)
C4 H4 0.9500
C5 C6 1.4039(13)
C5 C8 1.4625(13)
C6 C7 1.3858(13)
C6 H6 0.9500
C7 H7 0.9500
C8 C12 1.3520(12)
C8 O1 1.3770(11)
C9 O2 1.2083(12)
C9 O1 1.3788(11)
C9 C10 1.4686(12)
C10 N1 1.3682(12)
C10 C11 1.3721(12)
C11 C12 1.4180(13)
C11 H11 0.9500
C12 H12 0.9500
C13 N1 1.4794(12)
C13 C14 1.5310(13)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.5308(14)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.5169(14)
C15 H15A 0.9900
C15 H15B 0.9900
C16 N1 1.4643(12)
C16 H16A 0.9900
C16 H16B 0.9900
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 C2 C3 C4 -0.45(13)
C1 C2 C3 C4 -179.95(8)
C2 C3 C4 C5 0.60(14)
C3 C4 C5 C6 -0.02(13)
C3 C4 C5 C8 -177.85(8)
C4 C5 C6 C7 -0.69(13)
C8 C5 C6 C7 177.15(8)
C5 C6 C7 C2 0.86(14)
C3 C2 C7 C6 -0.28(13)
C1 C2 C7 C6 179.23(8)
C4 C5 C8 C12 167.94(9)
C6 C5 C8 C12 -9.83(14)
C4 C5 C8 O1 -8.64(12)
C6 C5 C8 O1 173.58(8)
O2 C9 C10 N1 1.19(15)
O1 C9 C10 N1 -177.56(8)
O2 C9 C10 C11 175.32(10)
O1 C9 C10 C11 -3.43(12)
N1 C10 C11 C12 174.15(9)
C9 C10 C11 C12 0.39(14)
O1 C8 C12 C11 -0.07(14)
C5 C8 C12 C11 -176.47(9)
C10 C11 C12 C8 1.43(14)
N1 C13 C14 C15 -23.45(10)
C13 C14 C15 C16 37.75(10)
C14 C15 C16 N1 -37.35(10)
C11 C10 N1 C16 0.26(14)
C9 C10 N1 C16 174.04(8)
C11 C10 N1 C13 152.11(9)
C9 C10 N1 C13 -34.11(13)
C15 C16 N1 C10 179.32(8)
C15 C16 N1 C13 23.82(10)
C14 C13 N1 C10 -153.91(9)
C14 C13 N1 C16 -0.15(10)
C12 C8 O1 C9 -3.35(13)
C5 C8 O1 C9 173.57(8)
O2 C9 O1 C8 -173.83(9)
C10 C9 O1 C8 5.04(12)
