#------------------------------------------------------------------------------
#$Date: 2019-10-28 11:24:59 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220032 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/48/4514874.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_4514874
loop_
_publ_author_name
'Yang, Junfeng'
'Sun, Qiao'
'Yoshikai, Naohiko'
_publ_section_title
;
 Cobalt-Catalyzed Regio- and Diastereoselective Formal [3 + 2]
 Cycloaddition between Cyclopropanols and Allenes
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              1973
_journal_paper_doi               10.1021/acscatal.8b05114
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C19 H26 O'
_chemical_formula_weight         270.40
_space_group_crystal_system      tetragonal
_space_group_IT_number           120
_space_group_name_Hall           'I -4 -2c'
_space_group_name_H-M_alt        'I -4 c 2'
_symmetry_space_group_name_Hall  'I -4 -2c'
_symmetry_space_group_name_H-M   'I -4 c 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.4852(8)
_cell_length_b                   15.4852(8)
_cell_length_c                   26.1457(16)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      22.3255
_cell_measurement_theta_min      2.4263
_cell_volume                     6269.5(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23364
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.43
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.158
_refine_ls_abs_structure_details
;

Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0435P)²+2.4296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                2568
_reflns_number_total             3233
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b05114_si_002.cif
_cod_data_source_block           yoshi81m
_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/current/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 
;
_cod_original_cell_volume        6269.5(8)
_cod_database_code               4514874
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z+1/2'
'-x, y, z+1/2'
'y, x, -z+1/2'
'-y, -x, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1'
'-x+1/2, y+1/2, z+1'
'y+1/2, x+1/2, -z+1'
'-y+1/2, -x+1/2, -z+1'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.56422(17) 0.44336(16) 0.69913(9) 0.0380(6) Uani d . . D 1 . .
H H1O 0.569(4) 0.430(4) 0.7284(11) 0.013(15) Uiso d . P D 0.5 A 1
H H2O 0.511(2) 0.446(6) 0.694(4) 0.10(4) Uiso d . P D 0.5 B 2
C C1 0.7197(2) 0.5712(2) 0.71403(12) 0.0348(8) Uani d . . . 1 . .
H H1 0.661773 0.573077 0.725873 0.042 Uiso calc U . R 1 . .
C C2 0.7841(2) 0.6095(2) 0.74273(13) 0.0366(8) Uani d . . . 1 . .
H H2 0.770068 0.637113 0.774079 0.044 Uiso calc U . R 1 . .
C C3 0.8685(2) 0.6078(2) 0.72623(12) 0.0359(8) Uani d . . . 1 . .
H H3 0.912618 0.634281 0.746039 0.043 Uiso calc U . R 1 . .
C C4 0.8885(2) 0.5675(2) 0.68072(13) 0.0346(8) Uani d . . . 1 . .
H H4 0.946538 0.566576 0.668925 0.041 Uiso calc U . R 1 . .
C C5 0.8237(2) 0.5282(2) 0.65203(12) 0.0312(7) Uani d . . . 1 . .
H H5 0.838263 0.499913 0.620973 0.037 Uiso calc U . R 1 . .
C C6 0.7384(2) 0.5297(2) 0.66796(11) 0.0272(7) Uani d . . . 1 . .
C C7 0.66776(19) 0.4883(2) 0.63584(11) 0.0268(7) Uani d . . . 1 . .
H H7A 0.693942 0.468296 0.603399 0.032 Uiso calc U . R 1 . .
H H7B 0.624991 0.533486 0.627101 0.032 Uiso calc U . R 1 . .
C C8 0.61924(19) 0.41206(19) 0.65990(10) 0.0233(6) Uani d . . . 1 . .
C C9 0.6791(2) 0.34238(19) 0.68070(11) 0.0284(7) Uani d . . . 1 . .
H H9A 0.728337 0.36823 0.69942 0.034 Uiso calc U . R 1 . .
H H9B 0.647762 0.302746 0.703872 0.034 Uiso calc U . R 1 . .
C C10 0.7099(2) 0.2953(2) 0.63293(13) 0.0341(8) Uani d . . . 1 . .
H H10A 0.716067 0.232701 0.6397 0.041 Uiso calc U . R 1 . .
H H10B 0.766275 0.318327 0.621427 0.041 Uiso calc U . R 1 . .
C C11 0.6404(2) 0.3115(2) 0.59266(12) 0.0287(7) Uani d . . . 1 . .
C C12 0.56973(19) 0.3643(2) 0.61674(11) 0.0241(6) Uani d . . . 1 . .
H H12 0.547398 0.407269 0.591407 0.029 Uiso calc U . R 1 . .
C C13 0.4946(2) 0.3079(2) 0.63632(11) 0.0270(7) Uani d . . . 1 . .
H H13A 0.518803 0.253201 0.649704 0.032 Uiso calc U . R 1 . .
H H13B 0.466531 0.338128 0.665243 0.032 Uiso calc U . R 1 . .
C C14 0.4252(2) 0.2861(2) 0.59620(12) 0.0323(7) Uani d . . . 1 . .
H H14A 0.368033 0.300136 0.610983 0.039 Uiso calc U . R 1 . .
H H14B 0.433878 0.324486 0.566366 0.039 Uiso calc U . R 1 . .
C C15 0.4223(2) 0.1927(2) 0.57684(13) 0.0343(8) Uani d . . . 1 . .
H H15A 0.411469 0.154805 0.606641 0.041 Uiso calc U . R 1 . .
H H15B 0.371895 0.187255 0.553798 0.041 Uiso calc U . R 1 . .
C C16 0.5003(2) 0.1578(2) 0.54883(12) 0.0372(8) Uani d . . . 1 . .
H H16A 0.489627 0.096208 0.540959 0.045 Uiso calc U . R 1 . .
H H16B 0.550416 0.160304 0.572323 0.045 Uiso calc U . R 1 . .
C C17 0.5252(3) 0.2033(2) 0.49934(12) 0.0437(10) Uani d . . . 1 . .
H H17A 0.471791 0.21517 0.479752 0.052 Uiso calc U . R 1 . .
H H17B 0.560788 0.163223 0.478692 0.052 Uiso calc U . R 1 . .
C C18 0.5753(3) 0.2888(3) 0.50551(12) 0.0454(10) Uani d . . . 1 . .
H H18A 0.601624 0.304769 0.472324 0.054 Uiso calc U . R 1 . .
H H18B 0.534607 0.335209 0.515336 0.054 Uiso calc U . R 1 . .
C C19 0.6449(2) 0.2817(2) 0.54531(12) 0.0391(9) Uani d . . . 1 . .
H H19 0.696796 0.253325 0.535622 0.047 Uiso calc U . R 1 . .
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
C8 O1 H1O 124.(4)
C8 O1 H2O 119.(7)
C2 C1 C6 121.1(3)
C2 C1 H1 119.4
C6 C1 H1 119.4
C3 C2 C1 120.5(3)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 119.5(3)
C2 C3 H3 120.3
C4 C3 H3 120.3
C3 C4 C5 120.0(3)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 121.2(3)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C1 117.7(3)
C5 C6 C7 120.8(3)
C1 C6 C7 121.5(3)
C6 C7 C8 116.8(2)
C6 C7 H7A 108.1
C8 C7 H7A 108.1
C6 C7 H7B 108.1
C8 C7 H7B 108.1
H7A C7 H7B 107.3
O1 C8 C9 110.5(2)
O1 C8 C7 109.1(2)
C9 C8 C7 113.2(3)
O1 C8 C12 113.1(2)
C9 C8 C12 102.9(2)
C7 C8 C12 108.1(2)
C10 C9 C8 103.7(2)
C10 C9 H9A 111.0
C8 C9 H9A 111.0
C10 C9 H9B 111.0
C8 C9 H9B 111.0
H9A C9 H9B 109.0
C9 C10 C11 105.5(2)
C9 C10 H10A 110.6
C11 C10 H10A 110.6
C9 C10 H10B 110.6
C11 C10 H10B 110.6
H10A C10 H10B 108.8
C19 C11 C12 128.3(3)
C19 C11 C10 123.5(3)
C12 C11 C10 108.3(2)
C11 C12 C13 112.3(2)
C11 C12 C8 101.7(2)
C13 C12 C8 113.6(2)
C11 C12 H12 109.6
C13 C12 H12 109.6
C8 C12 H12 109.6
C14 C13 C12 115.1(2)
C14 C13 H13A 108.5
C12 C13 H13A 108.5
C14 C13 H13B 108.5
C12 C13 H13B 108.5
H13A C13 H13B 107.5
C15 C14 C13 116.9(3)
C15 C14 H14A 108.1
C13 C14 H14A 108.1
C15 C14 H14B 108.1
C13 C14 H14B 108.1
H14A C14 H14B 107.3
C16 C15 C14 118.3(3)
C16 C15 H15A 107.7
C14 C15 H15A 107.7
C16 C15 H15B 107.7
C14 C15 H15B 107.7
H15A C15 H15B 107.1
C15 C16 C17 116.6(3)
C15 C16 H16A 108.1
C17 C16 H16A 108.1
C15 C16 H16B 108.1
C17 C16 H16B 108.1
H16A C16 H16B 107.3
C16 C17 C18 115.8(3)
C16 C17 H17A 108.3
C18 C17 H17A 108.3
C16 C17 H17B 108.3
C18 C17 H17B 108.3
H17A C17 H17B 107.4
C19 C18 C17 111.8(3)
C19 C18 H18A 109.3
C17 C18 H18A 109.3
C19 C18 H18B 109.3
C17 C18 H18B 109.3
H18A C18 H18B 107.9
C11 C19 C18 125.8(3)
C11 C19 H19 117.1
C18 C19 H19 117.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.419(3)
O1 H1O 0.79(2)
O1 H2O 0.84(3)
C1 C2 1.382(5)
C1 C6 1.395(4)
C1 H1 0.95
C2 C3 1.376(5)
C2 H2 0.95
C3 C4 1.379(5)
C3 H3 0.95
C4 C5 1.393(5)
C4 H4 0.95
C5 C6 1.385(4)
C5 H5 0.95
C6 C7 1.521(4)
C7 C8 1.534(4)
C7 H7A 0.99
C7 H7B 0.99
C8 C9 1.523(4)
C8 C12 1.552(4)
C9 C10 1.522(4)
C9 H9A 0.99
C9 H9B 0.99
C10 C11 1.526(5)
C10 H10A 0.99
C10 H10B 0.99
C11 C19 1.323(4)
C11 C12 1.505(4)
C12 C13 1.542(4)
C12 H12 1.0
C13 C14 1.540(4)
C13 H13A 0.99
C13 H13B 0.99
C14 C15 1.532(5)
C14 H14A 0.99
C14 H14B 0.99
C15 C16 1.513(5)
C15 H15A 0.99
C15 H15B 0.99
C16 C17 1.522(5)
C16 H16A 0.99
C16 H16B 0.99
C17 C18 1.543(5)
C17 H17A 0.99
C17 H17B 0.99
C18 C19 1.503(5)
C18 H18A 0.99
C18 H18B 0.99
C19 H19 0.95
