#------------------------------------------------------------------------------
#$Date: 2020-03-31 02:35:21 +0300 (Tue, 31 Mar 2020) $
#$Revision: 249840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038143.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_4038143
loop_
_publ_author_name
'Li, Zhenmin'
'Xie, Jianwei'
'Lu, Ping'
'Wang, Yanguang'
_publ_section_title
;
 Synthesis of 8-Alkoxy-5H-isochromeno[3,4-c]isoquinolines and
 1-Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C-H
 Functionalization of Benzimidates with 4-Diazoisochroman-3-imines and
 4-Diazoisoquinolin-3-ones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00283
_journal_year                    2020
_chemical_formula_moiety         'C22 H13 F2 N O'
_chemical_formula_sum            'C22 H13 F2 N O'
_chemical_formula_weight         345.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-03-01
_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            8
_cell_length_a                   16.8351(5)
_cell_length_b                   25.1745(8)
_cell_length_c                   7.2940(2)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      34.14
_cell_measurement_theta_min      2.71
_cell_volume                     3091.31(16)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            59672
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.366
_diffrn_reflns_theta_min         2.420
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1148 before and 0.0459 after correction.
The Ratio of minimum to maximum transmission is 0.9377.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         6491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0440
_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)+(0.0644P)²+0.8085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5221
_reflns_number_total             6491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00283_si_002.cif
_cod_data_source_block           190228_lzm7378_1_0ma_a
_cod_database_code               4038143
_shelx_shelxl_version_number     2016/6
_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   0.987
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
F1 F 0.08274(3) 0.61131(3) 0.10955(10) 0.03219(15) Uani 1 1 d . . . . .
F2 F 0.33933(4) 0.27085(3) 0.47329(13) 0.04210(19) Uani 1 1 d . . . . .
O1 O 0.50519(4) 0.56724(3) 0.16253(11) 0.02698(15) Uani 1 1 d . . . . .
N1 N 0.41797(4) 0.50277(3) 0.23428(11) 0.02259(15) Uani 1 1 d . . . . .
C1 C 0.49674(7) 0.70765(4) 0.06068(17) 0.0337(2) Uani 1 1 d . . . . .
H1 H 0.548653 0.713441 0.013679 0.040 Uiso 1 1 calc R . . . .
C2 C 0.45054(7) 0.75044(5) 0.11357(18) 0.0376(2) Uani 1 1 d . . . . .
H2 H 0.470029 0.785623 0.099764 0.045 Uiso 1 1 calc R . . . .
C3 C 0.37568(7) 0.74173(4) 0.18679(17) 0.0336(2) Uani 1 1 d . . . . .
H3 H 0.344460 0.771033 0.226046 0.040 Uiso 1 1 calc R . . . .
C4 C 0.34599(6) 0.69052(4) 0.20319(14) 0.02685(18) Uani 1 1 d . . . . .
H4 H 0.294987 0.685031 0.255608 0.032 Uiso 1 1 calc R . . . .
C5 C 0.39051(5) 0.64686(4) 0.14319(13) 0.02241(16) Uani 1 1 d . . . . .
C6 C 0.46751(6) 0.65628(4) 0.07605(13) 0.02572(18) Uani 1 1 d . . . . .
C7 C 0.51632(6) 0.60856(4) 0.02755(15) 0.02849(19) Uani 1 1 d . . . . .
H7A H 0.500406 0.595257 -0.094787 0.034 Uiso 1 1 calc R . . . .
H7B H 0.573143 0.618557 0.022102 0.034 Uiso 1 1 calc R . . . .
C8 C 0.42730(5) 0.55366(4) 0.18514(12) 0.02157(16) Uani 1 1 d . . . . .
C9 C 0.36700(5) 0.59078(3) 0.16396(12) 0.02007(15) Uani 1 1 d . . . . .
C10 C 0.28786(5) 0.57091(3) 0.17554(11) 0.01897(15) Uani 1 1 d . . . . .
C11 C 0.27580(5) 0.51698(3) 0.23016(12) 0.01910(14) Uani 1 1 d . . . . .
C12 C 0.34455(5) 0.48449(4) 0.25791(12) 0.02034(15) Uani 1 1 d . . . . .
C13 C 0.22040(5) 0.60229(4) 0.13245(13) 0.02156(16) Uani 1 1 d . . . . .
H13 H 0.226713 0.637596 0.088788 0.026 Uiso 1 1 calc R . . . .
C14 C 0.14648(5) 0.58125(4) 0.15437(13) 0.02279(16) Uani 1 1 d . . . . .
C15 C 0.13225(5) 0.53007(4) 0.22228(14) 0.02399(17) Uani 1 1 d . . . . .
H15 H 0.079711 0.517641 0.242693 0.029 Uiso 1 1 calc R . . . .
C16 C 0.19674(5) 0.49859(4) 0.25820(13) 0.02180(16) Uani 1 1 d . . . . .
H16 H 0.188519 0.463582 0.302971 0.026 Uiso 1 1 calc R . . . .
C17 C 0.34086(5) 0.42768(3) 0.31344(12) 0.02078(15) Uani 1 1 d . . . . .
C18 C 0.28967(6) 0.39119(4) 0.23003(14) 0.02516(17) Uani 1 1 d . . . . .
H18 H 0.254503 0.402858 0.136463 0.030 Uiso 1 1 calc R . . . .
C19 C 0.28957(6) 0.33811(4) 0.28224(16) 0.0297(2) Uani 1 1 d . . . . .
H19 H 0.254680 0.313343 0.225908 0.036 Uiso 1 1 calc R . . . .
C20 C 0.34139(6) 0.32236(4) 0.41778(16) 0.0293(2) Uani 1 1 d . . . . .
C21 C 0.39443(6) 0.35656(4) 0.50058(14) 0.02785(19) Uani 1 1 d . . . . .
H21 H 0.430144 0.344268 0.592064 0.033 Uiso 1 1 calc R . . . .
C22 C 0.39419(5) 0.40948(4) 0.44651(13) 0.02407(17) Uani 1 1 d . . . . .
H22 H 0.430702 0.433616 0.500575 0.029 Uiso 1 1 calc R . . . .
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 O1 C7 112.78(7) . . ?
C12 N1 C8 118.33(8) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.23(10) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.70(10) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.50(11) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.62(10) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.03(9) . . ?
C4 C5 C9 125.16(8) . . ?
C6 C5 C9 116.42(8) . . ?
C1 C6 C5 120.80(10) . . ?
C1 C6 C7 122.24(9) . . ?
C5 C6 C7 116.93(8) . . ?
O1 C7 C6 110.20(8) . . ?
O1 C7 H7A 109.6 . . ?
O1 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O1 C8 C9 121.34(8) . . ?
N1 C8 O1 112.62(8) . . ?
N1 C8 C9 126.00(8) . . ?
C8 C9 C5 117.38(8) . . ?
C8 C9 C10 116.13(8) . . ?
C10 C9 C5 126.38(8) . . ?
C9 C10 C11 118.85(7) . . ?
C13 C10 C9 122.66(8) . . ?
C13 C10 C11 118.48(7) . . ?
C10 C11 C12 117.86(7) . . ?
C16 C11 C10 118.79(8) . . ?
C16 C11 C12 123.33(8) . . ?
N1 C12 C11 122.36(8) . . ?
N1 C12 C17 114.00(8) . . ?
C11 C12 C17 123.64(8) . . ?
C10 C13 H13 120.4 . . ?
C14 C13 C10 119.26(8) . . ?
C14 C13 H13 120.4 . . ?
F1 C14 C13 118.60(8) . . ?
F1 C14 C15 117.65(8) . . ?
C13 C14 C15 123.75(8) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 C14 117.66(8) . . ?
C16 C15 H15 121.2 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.69(8) . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C12 122.59(8) . . ?
C18 C17 C22 118.81(8) . . ?
C22 C17 C12 118.48(8) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.87(9) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.23(9) . . ?
C20 C19 H19 120.9 . . ?
F2 C20 C19 118.20(10) . . ?
F2 C20 C21 118.79(9) . . ?
C19 C20 C21 123.00(9) . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.18(9) . . ?
C22 C21 H21 120.9 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.85(9) . . ?
C21 C22 H22 119.6 . . ?
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
F1 C14 1.3532(10) . ?
F2 C20 1.3590(12) . ?
O1 C7 1.4444(13) . ?
O1 C8 1.3653(10) . ?
N1 C8 1.3395(12) . ?
N1 C12 1.3301(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.3835(18) . ?
C1 C6 1.3883(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3863(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3877(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.4005(14) . ?
C5 C6 1.4058(13) . ?
C5 C9 1.4739(12) . ?
C6 C7 1.4978(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3885(12) . ?
C9 C10 1.4257(11) . ?
C10 C11 1.4295(12) . ?
C10 C13 1.4187(12) . ?
C11 C12 1.4318(12) . ?
C11 C16 1.4239(12) . ?
C12 C17 1.4875(13) . ?
C13 H13 0.9500 . ?
C13 C14 1.3619(12) . ?
C14 C15 1.4009(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.3694(13) . ?
C16 H16 0.9500 . ?
C17 C18 1.3988(13) . ?
C17 C22 1.3994(13) . ?
C18 H18 0.9500 . ?
C18 C19 1.3896(14) . ?
C19 H19 0.9500 . ?
C19 C20 1.3768(15) . ?
C20 C21 1.3798(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.3893(14) . ?
C22 H22 0.9500 . ?
