data_cu_20200707b_0m
_audit_creation_date               2020-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          none
_chemical_formula_moiety           '0.1(C27 H27 F N2 O3)'
_chemical_formula_sum              'C2.70 H2.70 F0.10 N0.20 O0.30'
_chemical_formula_weight           44.65
_chemical_absolute_configuration   unk
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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'
 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_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'

_cell_length_a                     10.0069(3)
_cell_length_b                     14.7854(5)
_cell_length_c                     16.3253(5)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2415.43(13)
_cell_formula_units_Z              40
_cell_measurement_reflns_used      9053
_cell_measurement_temperature      120
_cell_measurement_theta_max        68.28
_cell_measurement_theta_min        4.03
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.696
_exptl_absorpt_correction_T_max    0.7531
_exptl_absorpt_correction_T_min    0.5203
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1425 before and 0.0876 after correction. The Ratio of minimum to maximum transmission is 0.6909. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_lustre       .
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.228
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               944
_exptl_crystal_preparation         'as described in manuscript'
_exptl_crystal_recrystallization_method  'as described in manuscript'
_exptl_crystal_size_max            0.5
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0666
_diffrn_reflns_av_unetI/netI       0.0181
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         17
_diffrn_reflns_limit_k_min         -17
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              97609
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           68.331
_diffrn_reflns_theta_min           4.034
_diffrn_ambient_temperature        120.0
_diffrn_detector                   'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CCD area detector'
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device         'three-circle diffractometer'
_diffrn_measurement_device_type    'Bruker SMART APEX2 area detector'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_type                'Incoatec I\ms'
_diffrn_special_details            none
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.761
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       1.000
_reflns_number_gt                  4343
_reflns_number_total               4430
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.532
_refine_diff_density_min           -0.244
_refine_diff_density_rms           0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.06(3)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.101
_refine_ls_hydrogen_treatment      refall
_refine_ls_matrix_type             full
_refine_ls_number_parameters       406
_refine_ls_number_reflns           4430
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0342
_refine_ls_R_factor_gt             0.0334
_refine_ls_restrained_S_all        1.101
_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)+(0.0556P)²+0.4188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0870
_refine_ls_wR_factor_ref           0.0883
_refine_special_details            none
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 F001 F 0.65362(12) 0.53713(8) 0.69796(7) 0.0277(3) Uani 1 1 d . . . . .
 O002 O 0.73566(16) 0.33724(10) 0.59177(9) 0.0315(3) Uani 1 1 d . . . . .
 O003 O 0.68193(16) 0.64953(10) 0.54821(9) 0.0319(3) Uani 1 1 d . . . . .
 O004 O 0.90231(16) 0.55749(10) 0.66716(9) 0.0334(4) Uani 1 1 d . . . . .
 N005 N 0.60212(16) 0.50613(10) 0.56273(10) 0.0224(3) Uani 1 1 d . . . . .
 N006 N 0.69135(19) 0.36774(12) 0.72572(11) 0.0276(4) Uani 1 1 d . . . . .
 C007 C 0.6045(2) 0.59110(13) 0.52512(12) 0.0244(4) Uani 1 1 d . . . . .
 C008 C 0.4754(2) 0.45890(13) 0.56908(12) 0.0225(4) Uani 1 1 d . . . . .
 C009 C 0.51611(19) 0.60430(13) 0.45277(12) 0.0237(4) Uani 1 1 d . . . . .
 C00A C 0.7087(2) 0.38943(13) 0.64727(12) 0.0232(4) Uani 1 1 d . . . . .
 C00B C 0.3722(2) 0.49698(13) 0.61424(12) 0.0245(4) Uani 1 1 d . . . . .
 C00C C 0.4523(2) 0.68712(14) 0.44266(12) 0.0262(4) Uani 1 1 d . . . . .
 C00D C 0.3773(2) 0.70378(14) 0.37243(13) 0.0295(4) Uani 1 1 d . . . . .
 C00E C 0.9037(2) 0.51965(14) 0.52693(13) 0.0276(4) Uani 1 1 d . . . . .
 C00F C 0.2292(2) 0.37034(14) 0.58091(13) 0.0284(4) Uani 1 1 d . . . . .
 C00G C 0.3684(2) 0.63833(15) 0.31188(13) 0.0293(4) Uani 1 1 d . . . . .
 C00H C 0.2502(2) 0.45279(14) 0.61962(13) 0.0272(4) Uani 1 1 d . . . . .
 C00I C 0.5069(2) 0.53876(14) 0.39179(13) 0.0277(4) Uani 1 1 d . . . . .
 C00J C 0.6869(2) 0.27386(14) 0.75846(13) 0.0289(5) Uani 1 1 d . . . . .
 C00K C 0.4567(2) 0.37621(14) 0.53007(13) 0.0299(4) Uani 1 1 d . . . . .
 C00L C 0.3343(2) 0.33254(14) 0.53630(14) 0.0316(5) Uani 1 1 d . . . . .
 C00M C 0.8557(2) 0.46457(15) 0.46363(13) 0.0295(4) Uani 1 1 d . . . . .
 C00N C 0.8409(2) 0.52801(13) 0.60950(12) 0.0258(4) Uani 1 1 d . . . . .
 C00O C 0.6969(2) 0.49198(13) 0.62716(11) 0.0233(4) Uani 1 1 d . . . . .
 C00P C 0.4343(2) 0.55604(15) 0.32109(13) 0.0308(4) Uani 1 1 d . . . . .
 C00Q C 0.9253(3) 0.45895(18) 0.39019(14) 0.0374(5) Uani 1 1 d . . . . .
 C00R C 1.0220(2) 0.56862(17) 0.51495(16) 0.0370(5) Uani 1 1 d . . . . .
 C00S C 0.0963(2) 0.32286(19) 0.58607(17) 0.0400(5) Uani 1 1 d . . . . .
 C00T C 1.0424(3) 0.5075(2) 0.37947(17) 0.0490(6) Uani 1 1 d . . . . .
 C00U C 0.8143(3) 0.2228(2) 0.7363(2) 0.0530(7) Uani 1 1 d . . . . .
 C00V C 0.6810(4) 0.28257(19) 0.85111(16) 0.0523(8) Uani 1 1 d . . . . .
 C00W C 1.0905(3) 0.5619(2) 0.44125(18) 0.0494(7) Uani 1 1 d . . . . .
 C00X C 0.5646(4) 0.2275(2) 0.7244(2) 0.0566(9) Uani 1 1 d . . . . .
 H00B H 0.383(3) 0.556(2) 0.6386(19) 0.044(8) Uiso 1 1 d . . . . .
 H00P H 0.429(3) 0.504(2) 0.2812(17) 0.038(7) Uiso 1 1 d . . . . .
 H00H H 0.175(3) 0.485(2) 0.6505(17) 0.040(7) Uiso 1 1 d . . . . .
 H00I H 0.558(3) 0.481(2) 0.3988(18) 0.040(7) Uiso 1 1 d . . . . .
 H00M H 0.775(3) 0.4267(17) 0.4715(15) 0.026(6) Uiso 1 1 d . . . . .
 H00K H 0.531(3) 0.3482(19) 0.4986(17) 0.037(7) Uiso 1 1 d . . . . .
 H00D H 0.325(3) 0.7614(18) 0.3666(16) 0.030(6) Uiso 1 1 d . . . . .
 H00G H 0.316(3) 0.6477(19) 0.2611(18) 0.037(7) Uiso 1 1 d . . . . .
 H00W H 1.171(4) 0.602(3) 0.436(2) 0.072(11) Uiso 1 1 d . . . . .
 H00Q H 0.897(4) 0.419(2) 0.350(2) 0.056(9) Uiso 1 1 d . . . . .
 H00T H 1.097(4) 0.503(3) 0.326(2) 0.069(10) Uiso 1 1 d . . . . .
 H00C H 0.460(3) 0.7339(19) 0.4848(18) 0.037(7) Uiso 1 1 d . . . . .
 H00A H 0.060(4) 0.319(2) 0.530(2) 0.061(10) Uiso 1 1 d . . . . .
 H00J H 0.814(4) 0.162(3) 0.764(2) 0.058(9) Uiso 1 1 d . . . . .
 H00X H 0.553(4) 0.166(3) 0.746(2) 0.065(10) Uiso 1 1 d . . . . .
 H00R H 1.054(3) 0.606(2) 0.5583(19) 0.043(8) Uiso 1 1 d . . . . .
 H00E H 0.109(4) 0.259(3) 0.602(2) 0.067(10) Uiso 1 1 d . . . . .
 H00S H 0.669(4) 0.221(3) 0.878(2) 0.069(11) Uiso 1 1 d . . . . .
 H00L H 0.320(4) 0.273(3) 0.507(2) 0.070(11) Uiso 1 1 d . . . . .
 H00N H 0.822(4) 0.217(2) 0.672(2) 0.057(9) Uiso 1 1 d . . . . .
 H00F H 0.033(4) 0.355(2) 0.624(2) 0.058(9) Uiso 1 1 d . . . . .
 H00U H 0.599(4) 0.315(3) 0.862(2) 0.058(10) Uiso 1 1 d . . . . .
 H00Y H 0.569(4) 0.221(3) 0.663(3) 0.074(11) Uiso 1 1 d . . . . .
 H006 H 0.664(3) 0.412(2) 0.759(2) 0.049(9) Uiso 1 1 d . . . . .
 H H 0.481(6) 0.266(3) 0.742(3) 0.102(16) Uiso 1 1 d . . . . .
 H00V H 0.760(7) 0.314(5) 0.877(4) 0.14(2) Uiso 1 1 d . . . . .
 H00O H 0.899(4) 0.262(3) 0.754(3) 0.073(12) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 F001 C00O 1.403(2) . ?
 O002 C00A 1.220(3) . ?
 O003 C007 1.220(3) . ?
 O004 C00N 1.206(3) . ?
 N005 C007 1.398(2) . ?
 N005 C008 1.452(2) . ?
 N005 C00O 1.431(2) . ?
 N006 C00A 1.332(3) . ?
 N006 C00J 1.488(3) . ?
 C007 C009 1.489(3) . ?
 C008 C00B 1.388(3) . ?
 C008 C00K 1.391(3) . ?
 C009 C00C 1.391(3) . ?
 C009 C00I 1.392(3) . ?
 C00A C00O 1.556(3) . ?
 C00B C00H 1.388(3) . ?
 C00C C00D 1.392(3) . ?
 C00D C00G 1.386(3) . ?
 C00E C00M 1.401(3) . ?
 C00E C00N 1.492(3) . ?
 C00E C00R 1.401(3) . ?
 C00F C00H 1.389(3) . ?
 C00F C00L 1.395(3) . ?
 C00F C00S 1.507(3) . ?
 C00G C00P 1.392(3) . ?
 C00I C00P 1.388(3) . ?
 C00J C00U 1.525(4) . ?
 C00J C00V 1.519(3) . ?
 C00J C00X 1.509(3) . ?
 C00K C00L 1.389(3) . ?
 C00M C00Q 1.389(3) . ?
 C00N C00O 1.563(3) . ?
 C00Q C00T 1.385(4) . ?
 C00R C00W 1.388(4) . ?
 C00T C00W 1.377(5) . ?

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
 C007 N005 C008 118.59(16) . . ?
 C007 N005 C00O 116.27(16) . . ?
 C00O N005 C008 117.12(15) . . ?
 C00A N006 C00J 125.04(17) . . ?
 O003 C007 N005 120.76(18) . . ?
 O003 C007 C009 121.98(18) . . ?
 N005 C007 C009 117.12(16) . . ?
 C00B C008 N005 119.52(17) . . ?
 C00B C008 C00K 119.99(19) . . ?
 C00K C008 N005 120.49(18) . . ?
 C00C C009 C007 118.86(18) . . ?
 C00C C009 C00I 119.84(19) . . ?
 C00I C009 C007 121.01(18) . . ?
 O002 C00A N006 126.19(19) . . ?
 O002 C00A C00O 118.46(17) . . ?
 N006 C00A C00O 115.32(17) . . ?
 C00H C00B C008 119.81(18) . . ?
 C009 C00C C00D 120.06(19) . . ?
 C00G C00D C00C 119.91(19) . . ?
 C00M C00E C00N 124.72(18) . . ?
 C00M C00E C00R 119.2(2) . . ?
 C00R C00E C00N 116.1(2) . . ?
 C00H C00F C00L 118.38(19) . . ?
 C00H C00F C00S 121.1(2) . . ?
 C00L C00F C00S 120.5(2) . . ?
 C00D C00G C00P 120.2(2) . . ?
 C00B C00H C00F 121.14(19) . . ?
 C00P C00I C009 120.07(19) . . ?
 N006 C00J C00U 110.55(19) . . ?
 N006 C00J C00V 106.24(18) . . ?
 N006 C00J C00X 108.41(19) . . ?
 C00V C00J C00U 108.1(2) . . ?
 C00X C00J C00U 111.5(3) . . ?
 C00X C00J C00V 111.9(3) . . ?
 C00L C00K C008 119.6(2) . . ?
 C00K C00L C00F 121.10(19) . . ?
 C00Q C00M C00E 120.0(2) . . ?
 O004 C00N C00E 121.35(19) . . ?
 O004 C00N C00O 116.68(18) . . ?
 C00E C00N C00O 121.79(17) . . ?
 F001 C00O N005 109.36(16) . . ?
 F001 C00O C00A 108.27(15) . . ?
 F001 C00O C00N 105.91(15) . . ?
 N005 C00O C00A 110.36(15) . . ?
 N005 C00O C00N 115.16(15) . . ?
 C00A C00O C00N 107.50(16) . . ?
 C00I C00P C00G 119.9(2) . . ?
 C00T C00Q C00M 120.2(2) . . ?
 C00W C00R C00E 120.1(2) . . ?
 C00W C00T C00Q 120.4(2) . . ?
 C00T C00W C00R 120.3(2) . . ?

_olex2_exptl_crystal_mounting_method  'as described in manuscript'
_olex2_submission_special_instructions  'No special instructions were received'
