#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:35:48 +0300 (Mon, 04 May 2020) $
#$Revision: 251456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/46/4134681.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_4134681
loop_
_publ_author_name
'Nisbet, Matthew L.'
'Pendleton, Ian M.'
'Nolis, Gene M.'
'Griffith, Kent J.'
'Schrier, Joshua'
'Cabana, Jordi'
'Norquist, Alexander J.'
'Poeppelmeier, Kenneth R.'
_publ_section_title
;
 Machine-Learning-Assisted Synthesis of Polar Racemates.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7555
_journal_page_last               7566
_journal_paper_doi               10.1021/jacs.0c01239
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C10 H12 Cu F6 N2 O2 Ti'
_chemical_formula_sum            'C10 H12 Cu F6 N2 O2 Ti'
_chemical_formula_weight         417.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.72700(10)
_cell_length_b                   14.3219(3)
_cell_length_c                   12.3521(3)
_cell_measurement_reflns_used    6226
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.18
_cell_volume                     1366.95(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2017)'
_computing_data_collection       'APEX2 V2017.3 (Bruker, 2017)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.97
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10710
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         2.177
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.217
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0612 before and 0.0457 after correction. The Ratio of minimum to maximum transmission is 0.9060. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0225
_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)+(0.0312P)²+0.7563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1927
_reflns_number_total             2121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c01239_si_006.cif
_cod_data_source_block           work
_cod_depositor_comments
'Adding full bibliography for 4134676--4134681.cif.'
_cod_database_code               4134681
_shelx_shelxl_version_number     2018/3
_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_max   0.924
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.80945(3) 0.750000 0.54038(2) 0.00702(7) Uani 1 2 d S T P . .
Ti1 Ti 0.30652(4) 0.750000 0.55859(3) 0.00803(8) Uani 1 2 d S T P . .
F1 F 0.23759(12) 0.65590(7) 0.47253(7) 0.01681(19) Uani 1 1 d . . . . .
F2 F 0.52676(14) 0.750000 0.49424(9) 0.0102(2) Uani 1 2 d S T P . .
F3 F 0.39843(11) 0.84006(6) 0.66182(6) 0.01109(16) Uani 1 1 d . . . . .
F4 F 0.09741(15) 0.750000 0.63382(10) 0.0135(2) Uani 1 2 d S T P . .
O1 O 0.74712(14) 0.84909(7) 0.64626(8) 0.01035(19) Uani 1 1 d . . . . .
H1A H 0.646(3) 0.8438(17) 0.6542(19) 0.034(7) Uiso 1 1 d . . . . .
H1B H 0.796(3) 0.8495(17) 0.7020(19) 0.026(6) Uiso 1 1 d . . . . .
N1 N 0.86515(15) 0.65905(8) 0.42442(9) 0.0081(2) Uani 1 1 d . . . . .
C1 C 0.85620(18) 0.56598(10) 0.43186(11) 0.0105(2) Uani 1 1 d . . . . .
H1 H 0.821(2) 0.5425(15) 0.4957(18) 0.020(5) Uiso 1 1 d . . . . .
C2 C 0.90304(19) 0.50762(10) 0.34660(11) 0.0122(3) Uani 1 1 d . . . . .
H2 H 0.899(3) 0.4435(14) 0.3556(15) 0.014(4) Uiso 1 1 d . . . . .
C3 C 0.9595(2) 0.54794(10) 0.25050(11) 0.0130(3) Uani 1 1 d . . . . .
H3 H 0.991(3) 0.5085(14) 0.1909(15) 0.019(5) Uiso 1 1 d . . . . .
C4 C 0.96684(19) 0.64450(10) 0.24212(11) 0.0110(3) Uani 1 1 d . . . . .
H4 H 1.004(3) 0.6764(15) 0.1782(17) 0.027(6) Uiso 1 1 d . . . . .
C5 C 0.91935(16) 0.69847(9) 0.33042(10) 0.0079(2) 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Ti Ti 0.2776 0.4457 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 F2 86.08(4) . . ?
O1 Cu1 F2 86.08(4) 7_575 . ?
O1 Cu1 O1 91.04(6) . 7_575 ?
N1 Cu1 F2 91.58(4) . . ?
N1 Cu1 F2 91.58(4) 7_575 . ?
N1 Cu1 O1 93.37(4) . 7_575 ?
N1 Cu1 O1 174.86(4) 7_575 7_575 ?
N1 Cu1 O1 174.86(4) . . ?
N1 Cu1 O1 93.37(4) 7_575 . ?
N1 Cu1 N1 82.11(7) 7_575 . ?
F1 Ti1 F1 97.16(6) . 7_575 ?
F1 Ti1 F2 91.05(4) . . ?
F1 Ti1 F2 91.05(4) 7_575 . ?
F1 Ti1 F3 172.67(4) . . ?
F1 Ti1 F3 89.93(4) . 7_575 ?
F1 Ti1 F3 172.67(4) 7_575 7_575 ?
F1 Ti1 F3 89.93(4) 7_575 . ?
F1 Ti1 F4 92.18(4) 7_575 . ?
F1 Ti1 F4 92.18(4) . . ?
F2 Ti1 F3 86.94(4) . 7_575 ?
F2 Ti1 F3 86.94(4) . . ?
F3 Ti1 F3 82.93(5) 7_575 . ?
F4 Ti1 F2 175.13(5) . . ?
F4 Ti1 F3 89.41(4) . . ?
F4 Ti1 F3 89.41(4) . 7_575 ?
Ti1 F2 Cu1 140.34(6) . . ?
Ti1 F4 Cu1 122.68(6) . 1_455 ?
Cu1 O1 H1A 104.6(17) . . ?
Cu1 O1 H1B 117.6(17) . . ?
H1A O1 H1B 112(2) . . ?
C1 N1 Cu1 126.41(9) . . ?
C1 N1 C5 119.28(12) . . ?
C5 N1 Cu1 114.30(9) . . ?
N1 C1 H1 116.6(14) . . ?
N1 C1 C2 122.18(13) . . ?
C2 C1 H1 121.2(14) . . ?
C1 C2 H2 119.7(12) . . ?
C3 C2 C1 118.56(13) . . ?
C3 C2 H2 121.7(12) . . ?
C2 C3 H3 119.4(12) . . ?
C4 C3 C2 119.36(13) . . ?
C4 C3 H3 121.3(12) . . ?
C3 C4 H4 123.3(13) . . ?
C5 C4 C3 119.08(13) . . ?
C5 C4 H4 117.6(13) . . ?
N1 C5 C4 121.52(12) . . ?
N1 C5 C5 114.58(7) . 7_575 ?
C4 C5 C5 123.89(8) . 7_575 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 F2 2.2575(11) . ?
Cu1 O1 1.9891(10) 7_575 ?
Cu1 O1 1.9890(10) . ?
Cu1 N1 1.9833(11) 7_575 ?
Cu1 N1 1.9833(11) . ?
Ti1 F1 1.7972(9) 7_575 ?
Ti1 F1 1.7971(9) . ?
Ti1 F2 1.8783(12) . ?
Ti1 F3 1.9479(8) . ?
Ti1 F3 1.9478(8) 7_575 ?
Ti1 F4 1.8639(12) . ?
O1 H1A 0.79(3) . ?
O1 H1B 0.79(2) . ?
N1 C1 1.3379(18) . ?
N1 C5 1.3574(16) . ?
C1 H1 0.90(2) . ?
C1 C2 1.3924(19) . ?
C2 H2 0.925(19) . ?
C2 C3 1.390(2) . ?
C3 H3 0.960(19) . ?
C3 C4 1.388(2) . ?
C4 H4 0.96(2) . ?
C4 C5 1.3862(18) . ?
C5 C5 1.476(3) 7_575 ?
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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A F3 0.79(3) 1.92(3) 2.7042(14) 174(2) . yes
O1 H1B F3 0.79(2) 1.86(2) 2.6465(13) 174(2) 6_657 yes
