#------------------------------------------------------------------------------
#$Date: 2017-05-06 00:33:55 +0300 (Sat, 06 May 2017) $
#$Revision: 196281 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/98/7119886.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_7119886
loop_
_publ_author_name
'Min, Junxiang'
'Xu, Guangyang'
'Sun, Jiangtao'
_publ_section_title
;
 A controlled selective synthesis of dihydropyrans through tandem reaction
 of alkynes with diazo compounds.
;
_journal_issue                   31
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4350
_journal_page_last               4353
_journal_paper_doi               10.1039/c7cc01616f
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-01-18 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.308(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.392(3)
_cell_length_b                   9.3651(19)
_cell_length_c                   14.198(3)
_cell_measurement_reflns_used    2483
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      2.61
_cell_volume                     1769.9(7)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9867
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         1.530
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1026P)²+0.0679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2195
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc01616f2.cif
_cod_data_source_block           mjx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7119886.cif.
;
_cod_original_cell_volume        1769.9(6)
_cod_database_code               7119886
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.71132(16) -0.1183(2) 0.33914(15) 0.0526(6) Uani 1 1 d . .
H1 H 0.6801 -0.2060 0.3263 0.063 Uiso 1 1 calc R U
C2 C 0.80481(19) -0.1124(3) 0.39194(18) 0.0699(8) Uani 1 1 d . .
H2 H 0.8360 -0.1966 0.4139 0.084 Uiso 1 1 calc R U
C3 C 0.8515(2) 0.0146(4) 0.41210(18) 0.0735(8) Uani 1 1 d . .
H3 H 0.9137 0.0171 0.4482 0.088 Uiso 1 1 calc R U
C4 C 0.80638(17) 0.1391(3) 0.37896(18) 0.0677(7) Uani 1 1 d . .
H4 H 0.8384 0.2261 0.3921 0.081 Uiso 1 1 calc R U
C5 C 0.71323(16) 0.1352(3) 0.32598(16) 0.0550(6) Uani 1 1 d . .
H5 H 0.6828 0.2198 0.3038 0.066 Uiso 1 1 calc R U
C6 C 0.66487(15) 0.0059(2) 0.30574(14) 0.0404(5) Uani 1 1 d . .
C7 C 0.56340(14) -0.0010(2) 0.24668(14) 0.0391(5) Uani 1 1 d . .
H7 H 0.5522 -0.1007 0.2273 0.047 Uiso 1 1 calc R U
C8 C 0.56621(14) 0.0864(2) 0.15691(13) 0.0409(5) Uani 1 1 d . .
C9 C 0.6279(2) 0.0879(3) 0.00698(16) 0.0760(8) Uani 1 1 d . .
H9A H 0.5647 0.1269 -0.0197 0.114 Uiso 1 1 calc R U
H9B H 0.6518 0.0214 -0.0368 0.114 Uiso 1 1 calc R U
H9C H 0.6758 0.1636 0.0193 0.114 Uiso 1 1 calc R U
C10 C 0.47663(14) 0.0428(2) 0.29890(14) 0.0393(5) Uani 1 1 d . .
C11 C 0.47727(15) 0.1038(2) 0.38260(15) 0.0503(6) Uani 1 1 d . .
H11 H 0.5384 0.1288 0.4161 0.060 Uiso 1 1 calc R U
C12 C 0.38251(16) 0.1335(3) 0.42472(15) 0.0585(6) Uani 1 1 d . .
H12A H 0.3605 0.2304 0.4098 0.070 Uiso 1 1 calc R U
H12B H 0.3938 0.1241 0.4931 0.070 Uiso 1 1 calc R U
C13 C 0.30311(18) 0.0294(3) 0.38539(16) 0.0600(7) Uani 1 1 d . .
H13A H 0.3183 -0.0643 0.4123 0.072 Uiso 1 1 calc R U
H13B H 0.2385 0.0591 0.4035 0.072 Uiso 1 1 calc R U
C14 C 0.29732(16) 0.0207(2) 0.28015(15) 0.0435(5) Uani 1 1 d . .
C15 C 0.21647(15) 0.0128(2) 0.21773(15) 0.0470(5) Uani 1 1 d . .
H15 H 0.2271 0.0019 0.1545 0.056 Uiso 1 1 calc R U
C16 C 0.11239(16) 0.0195(2) 0.23853(16) 0.0504(6) Uani 1 1 d . .
C18 C -0.05776(18) 0.0121(3) 0.1637(2) 0.0776(9) Uani 1 1 d . .
H18 H -0.0725 -0.0075 0.2285 0.093 Uiso 1 1 calc R U
C19 C -0.0898(2) 0.1577(4) 0.1363(3) 0.1314(16) Uani 1 1 d . .
H19A H -0.0474 0.2254 0.1722 0.197 Uiso 1 1 calc R U
H19B H -0.1582 0.1716 0.1489 0.197 Uiso 1 1 calc R U
H19C H -0.0850 0.1713 0.0699 0.197 Uiso 1 1 calc R U
C20 C -0.1055(2) -0.0987(4) 0.0980(3) 0.1099(12) Uani 1 1 d . .
H20A H -0.0944 -0.0756 0.0341 0.165 Uiso 1 1 calc R U
H20B H -0.1763 -0.1017 0.1030 0.165 Uiso 1 1 calc R U
H20C H -0.0764 -0.1902 0.1147 0.165 Uiso 1 1 calc R U
O1 O 0.61467(12) 0.01511(16) 0.09469(10) 0.0565(5) Uani 1 1 d . .
O2 O 0.53282(12) 0.20335(18) 0.14295(11) 0.0688(5) Uani 1 1 d . .
O3 O 0.38773(10) 0.01006(15) 0.24283(10) 0.0496(4) Uani 1 1 d . .
O4 O 0.05012(12) 0.0029(2) 0.15846(12) 0.0694(6) Uani 1 1 d . .
O5 O 0.08260(12) 0.0356(2) 0.31444(13) 0.0829(6) 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'
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
C6 C1 C2 119.9(2)
C6 C1 H1 120.1
C2 C1 H1 120.1
C3 C2 C1 121.0(2)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 119.8(2)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C5 120.0(3)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 120.5(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.8(2)
C1 C6 C7 119.81(18)
C5 C6 C7 121.35(18)
C10 C7 C8 111.01(16)
C10 C7 C6 114.19(16)
C8 C7 C6 109.73(16)
C10 C7 H7 107.2
C8 C7 H7 107.2
C6 C7 H7 107.2
O2 C8 O1 123.51(19)
O2 C8 C7 126.28(18)
O1 C8 C7 110.19(17)
O1 C9 H9A 109.5
O1 C9 H9B 109.5
H9A C9 H9B 109.5
O1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 O3 122.13(18)
C11 C10 C7 129.40(18)
O3 C10 C7 108.47(16)
C10 C11 C12 121.49(19)
C10 C11 H11 119.3
C12 C11 H11 119.3
C11 C12 C13 109.22(18)
C11 C12 H12A 109.8
C13 C12 H12A 109.8
C11 C12 H12B 109.8
C13 C12 H12B 109.8
H12A C12 H12B 108.3
C14 C13 C12 111.39(19)
C14 C13 H13A 109.3
C12 C13 H13A 109.3
C14 C13 H13B 109.3
C12 C13 H13B 109.3
H13A C13 H13B 108.0
C15 C14 O3 115.29(18)
C15 C14 C13 128.6(2)
O3 C14 C13 116.01(18)
C14 C15 C16 126.3(2)
C14 C15 H15 116.9
C16 C15 H15 116.9
O5 C16 O4 122.6(2)
O5 C16 C15 127.4(2)
O4 C16 C15 110.01(18)
O4 C18 C19 107.7(2)
O4 C18 C20 106.6(2)
C19 C18 C20 112.8(3)
O4 C18 H18 109.8
C19 C18 H18 109.8
C20 C18 H18 109.8
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C8 O1 C9 116.68(19)
C14 O3 C10 119.79(15)
C16 O4 C18 118.50(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.379(3)
C1 C2 1.388(3)
C1 H1 0.9300
C2 C3 1.359(4)
C2 H2 0.9300
C3 C4 1.372(4)
C3 H3 0.9300
C4 C5 1.385(3)
C4 H4 0.9300
C5 C6 1.388(3)
C5 H5 0.9300
C6 C7 1.518(3)
C7 C10 1.503(3)
C7 C8 1.519(3)
C7 H7 0.9800
C8 O2 1.191(2)
C8 O1 1.332(2)
C9 O1 1.447(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.318(3)
C10 O3 1.392(2)
C11 C12 1.487(3)
C11 H11 0.9300
C12 C13 1.504(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.490(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.324(3)
C14 O3 1.378(2)
C15 C16 1.458(3)
C15 H15 0.9300
C16 O5 1.199(3)
C16 O4 1.343(3)
C18 O4 1.457(3)
C18 C19 1.469(4)
C18 C20 1.491(4)
C18 H18 0.9800
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13B O5 0.97 2.33 3.014(3) 127.0
C13 H13B O5 0.97 2.33 3.014(3) 127.0
C13 H13B O5 0.97 2.33 3.014(3) 127.0
C13 H13B O5 0.97 2.33 3.014(3) 127.0
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
C6 C1 C2 C3 0.5(4)
C1 C2 C3 C4 -0.8(4)
C2 C3 C4 C5 0.6(4)
C3 C4 C5 C6 -0.2(4)
C2 C1 C6 C5 0.0(3)
C2 C1 C6 C7 179.02(19)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 C7 -179.2(2)
C1 C6 C7 C10 104.7(2)
C5 C6 C7 C10 -76.2(2)
C1 C6 C7 C8 -129.91(19)
C5 C6 C7 C8 49.1(3)
C10 C7 C8 O2 25.8(3)
C6 C7 C8 O2 -101.4(2)
C10 C7 C8 O1 -155.97(16)
C6 C7 C8 O1 76.9(2)
C8 C7 C10 C11 -114.3(2)
C6 C7 C10 C11 10.3(3)
C8 C7 C10 O3 64.9(2)
C6 C7 C10 O3 -170.46(15)
O3 C10 C11 C12 3.7(3)
C7 C10 C11 C12 -177.2(2)
C10 C11 C12 C13 26.3(3)
C11 C12 C13 C14 -48.6(3)
C12 C13 C14 C15 -139.1(2)
C12 C13 C14 O3 45.6(3)
O3 C14 C15 C16 179.33(18)
C13 C14 C15 C16 4.0(4)
C14 C15 C16 O5 1.4(4)
C14 C15 C16 O4 -177.8(2)
O2 C8 O1 C9 1.3(3)
C7 C8 O1 C9 -177.06(18)
C15 C14 O3 C10 168.28(18)
C13 C14 O3 C10 -15.7(3)
C11 C10 O3 C14 -10.1(3)
C7 C10 O3 C14 170.63(15)
O5 C16 O4 C18 3.2(4)
C15 C16 O4 C18 -177.5(2)
C19 C18 O4 C16 97.4(3)
C20 C18 O4 C16 -141.2(3)
