#------------------------------------------------------------------------------
#$Date: 2020-11-25 00:36:13 +0200 (Wed, 25 Nov 2020) $
#$Revision: 259237 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518263.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_4518263
loop_
_publ_author_name
'Liu, Tanggao'
'Xu, Fan'
'Liu, Xiaojuan'
'Huang, Zhiqing'
'Long, Lipeng'
'Xu, Guohai'
'Xiao, Hong'
'Chen, Zhengwang'
_publ_section_title
;
 Switching the Regioselectivity Access to Pyrroles and Isoquinolines from
 Ketoxime Acetates and Ynals
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c05272
_journal_year                    2020
_chemical_formula_moiety         'C19 H14 F N O2'
_chemical_formula_sum            'C19 H14 F N O2'
_chemical_formula_weight         307.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.6830(10)
_cell_angle_beta                 62.7520(10)
_cell_angle_gamma                75.3920(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2551(4)
_cell_length_b                   9.7521(4)
_cell_length_c                   9.9640(5)
_cell_measurement_reflns_used    6328
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      2.909
_cell_volume                     771.56(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11154
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         2.988
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       strip
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0454
_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)+(0.0503P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2713
_reflns_number_total             3456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c05272_si_003.cif
_cod_data_source_block           cjl20200806sy_0m
_cod_database_code               4518263
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C13(H13), C17(H17), C1(H1), C16(H16), C5(H5), C14(H14),
 C2(H2), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O2 O 0.39685(13) 0.32591(14) 0.69204(13) 0.0657(3) Uani 1 1 d . . . . .
N1 N 0.15950(14) 0.28341(12) 0.89572(13) 0.0415(3) Uani 1 1 d . . . . .
F1 F -0.19392(14) 0.18879(13) 0.49864(13) 0.0784(3) Uani 1 1 d . . . . .
C6 C 0.37482(16) 0.25824(15) 1.14789(15) 0.0425(3) Uani 1 1 d . . . . .
O1 O 0.32631(18) 0.43757(13) 0.97216(16) 0.0724(4) Uani 1 1 d . . . . .
C18 C 0.25201(18) 0.36443(15) 0.75926(17) 0.0453(3) Uani 1 1 d . . . . .
C7 C 0.30175(18) 0.32248(15) 1.04015(16) 0.0456(3) Uani 1 1 d . . . . .
C12 C -0.02954(16) 0.22207(14) 0.80778(16) 0.0409(3) Uani 1 1 d . . . . .
C9 C 0.08417(19) 0.16811(16) 1.12382(16) 0.0481(4) Uani 1 1 d . . . . .
H9 H 0.0794 0.1298 1.2179 0.058 Uiso 1 1 calc R . . . .
C8 C 0.19656(17) 0.24722(15) 1.01923(16) 0.0426(3) Uani 1 1 d . . . . .
C10 C -0.02156(19) 0.15525(17) 1.06420(16) 0.0500(4) Uani 1 1 d . . . . .
H10 H -0.1098 0.1076 1.1122 0.060 Uiso 1 1 calc R . . . .
C11 C 0.02680(16) 0.22480(15) 0.92269(16) 0.0422(3) Uani 1 1 d . . . . .
C13 C 0.08161(18) 0.18488(19) 0.66237(17) 0.0542(4) Uani 1 1 d . . . . .
H13 H 0.1948 0.1670 0.6350 0.065 Uiso 1 1 calc R . . . .
C17 C -0.19747(18) 0.24742(17) 0.84615(18) 0.0511(4) Uani 1 1 d . . . . .
H17 H -0.2737 0.2720 0.9433 0.061 Uiso 1 1 calc R . . . .
C1 C 0.41476(18) 0.11288(17) 1.17671(17) 0.0504(4) Uani 1 1 d . . . . .
H1 H 0.3902 0.0512 1.1324 0.061 Uiso 1 1 calc R . . . .
C16 C -0.25326(19) 0.23676(18) 0.7425(2) 0.0551(4) Uani 1 1 d . . . . .
H16 H -0.3661 0.2538 0.7687 0.066 Uiso 1 1 calc R . . . .
C5 C 0.4129(2) 0.34871(18) 1.21511(18) 0.0533(4) Uani 1 1 d . . . . .
H5 H 0.3886 0.4465 1.1951 0.064 Uiso 1 1 calc R . . . .
C14 C 0.0270(2) 0.1740(2) 0.55799(18) 0.0625(5) Uani 1 1 d . . . . .
H14 H 0.1020 0.1491 0.4606 0.075 Uiso 1 1 calc R . . . .
C15 C -0.1395(2) 0.20070(17) 0.60077(18) 0.0527(4) Uani 1 1 d . . . . .
C2 C 0.4913(2) 0.0593(2) 1.2716(2) 0.0636(5) Uani 1 1 d . . . . .
H2 H 0.5191 -0.0384 1.2899 0.076 Uiso 1 1 calc R . . . .
C4 C 0.4866(2) 0.2937(2) 1.3113(2) 0.0642(5) Uani 1 1 d . . . . .
H4 H 0.5095 0.3546 1.3579 0.077 Uiso 1 1 calc R . . . .
C3 C 0.5262(2) 0.1497(2) 1.3384(2) 0.0664(5) Uani 1 1 d . . . . .
H3 H 0.5770 0.1131 1.4025 0.080 Uiso 1 1 calc R . . . .
C19 C 0.1545(3) 0.4941(2) 0.7159(3) 0.0827(6) Uani 1 1 d . . . . .
H19A H 0.1404 0.5708 0.7719 0.124 Uiso 1 1 calc GR . . . .
H19B H 0.0479 0.4769 0.7380 0.124 Uiso 1 1 calc GR . . . .
H19C H 0.2119 0.5189 0.6095 0.124 Uiso 1 1 calc GR . . . .
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'
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'
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
C8 N1 C18 124.47(11) . . ?
C11 N1 C18 126.54(12) . . ?
C11 N1 C8 108.94(11) . . ?
C1 C6 C7 122.70(13) . . ?
C1 C6 C5 119.10(14) . . ?
C5 C6 C7 118.10(13) . . ?
O2 C18 N1 119.64(13) . . ?
O2 C18 C19 124.58(15) . . ?
N1 C18 C19 115.77(14) . . ?
O1 C7 C6 120.77(13) . . ?
O1 C7 C8 120.16(14) . . ?
C8 C7 C6 119.05(12) . . ?
C13 C12 C11 121.45(12) . . ?
C17 C12 C11 119.99(13) . . ?
C17 C12 C13 118.40(13) . . ?
C8 C9 C10 108.03(13) . . ?
N1 C8 C7 120.82(12) . . ?
C9 C8 N1 107.25(12) . . ?
C9 C8 C7 129.30(13) . . ?
C11 C10 C9 108.35(13) . . ?
N1 C11 C12 123.86(12) . . ?
C10 C11 N1 107.40(12) . . ?
C10 C11 C12 128.10(13) . . ?
C14 C13 C12 121.03(14) . . ?
C16 C17 C12 120.98(14) . . ?
C6 C1 C2 120.02(15) . . ?
C15 C16 C17 118.54(14) . . ?
C4 C5 C6 120.17(16) . . ?
C15 C14 C13 118.44(15) . . ?
F1 C15 C16 118.75(14) . . ?
F1 C15 C14 118.65(15) . . ?
C16 C15 C14 122.60(15) . . ?
C3 C2 C1 120.23(17) . . ?
C3 C4 C5 120.18(16) . . ?
C4 C3 C2 120.28(17) . . ?
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
O2 C18 1.1835(18) . ?
N1 C18 1.4479(18) . ?
N1 C8 1.3880(18) . ?
N1 C11 1.3800(17) . ?
F1 C15 1.3580(17) . ?
C6 C7 1.487(2) . ?
C6 C1 1.384(2) . ?
C6 C5 1.392(2) . ?
O1 C7 1.2189(18) . ?
C18 C19 1.479(2) . ?
C7 C8 1.4598(19) . ?
C12 C11 1.4656(19) . ?
C12 C13 1.387(2) . ?
C12 C17 1.3852(19) . ?
C9 C8 1.374(2) . ?
C9 C10 1.395(2) . ?
C10 C11 1.372(2) . ?
C13 C14 1.377(2) . ?
C17 C16 1.378(2) . ?
C1 C2 1.384(2) . ?
C16 C15 1.362(2) . ?
C5 C4 1.379(2) . ?
C14 C15 1.364(2) . ?
C2 C3 1.370(3) . ?
C4 C3 1.369(3) . ?
