#------------------------------------------------------------------------------
#$Date: 2020-03-31 02:35:21 +0300 (Tue, 31 Mar 2020) $
#$Revision: 249840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038141.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_4038141
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         'C18 H14 Cl N O2'
_chemical_formula_sum            'C18 H14 Cl N O2'
_chemical_formula_weight         311.75
_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
_audit_creation_date             2018-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.418(2)
_cell_angle_beta                 99.192(2)
_cell_angle_gamma                116.633(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2025(4)
_cell_length_b                   8.5700(4)
_cell_length_c                   12.1558(6)
_cell_measurement_reflns_used    4986
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      2.76
_cell_volume                     726.73(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      169.98
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11362
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.549
_diffrn_reflns_theta_min         2.759
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.9081.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0477
_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)+(0.0441P)²+0.2484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3694
_reflns_number_total             4828
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00283_si_002.cif
_cod_data_source_block           181115_lzm7334_11_0m_a
_cod_database_code               4038141
_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   0.974
_shelx_estimated_absorpt_t_min   0.902
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
Cl1 Cl 0.85782(5) 0.80366(5) 0.85704(3) 0.03259(11) Uani 1 1 d . . . . .
O1 O 0.20902(15) 0.17167(14) 0.75836(9) 0.0278(2) Uani 1 1 d . . . . .
O2 O 0.39690(15) 0.10601(14) 0.43090(9) 0.0256(2) Uani 1 1 d . . . . .
N1 N 0.31070(17) 0.13993(17) 0.59987(11) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.7139(2) 0.4422(2) 0.50286(13) 0.0256(3) Uani 1 1 d . . . . .
H1 H 0.692672 0.362912 0.431231 0.031 Uiso 1 1 calc R . . . .
C2 C 0.8699(2) 0.6111(2) 0.54008(14) 0.0293(3) Uani 1 1 d . . . . .
H2 H 0.952538 0.651863 0.492123 0.035 Uiso 1 1 calc R . . . .
C3 C 0.9072(2) 0.7233(2) 0.64875(14) 0.0285(3) Uani 1 1 d . . . . .
H3 H 1.018717 0.837837 0.676256 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7830(2) 0.6682(2) 0.71582(13) 0.0244(3) Uani 1 1 d . . . . .
C5 C 0.6100(2) 0.50197(19) 0.67751(12) 0.0221(3) Uani 1 1 d . . . . .
C6 C 0.5848(2) 0.38614(19) 0.57078(12) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.4240(2) 0.20768(19) 0.53562(12) 0.0222(3) Uani 1 1 d . . . . .
C8 C 0.3364(2) 0.25440(19) 0.69942(13) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.4655(2) 0.43768(19) 0.73784(12) 0.0226(3) Uani 1 1 d . . . . .
C10 C 0.4144(2) 0.5463(2) 0.81797(12) 0.0241(3) Uani 1 1 d . . . . .
C11 C 0.3042(2) 0.4585(2) 0.88853(13) 0.0269(3) Uani 1 1 d . . . . .
C12 C 0.2654(2) 0.2681(2) 0.87912(13) 0.0288(3) Uani 1 1 d . . . . .
H12A H 0.380416 0.268523 0.919559 0.035 Uiso 1 1 calc R . . . .
H12B H 0.163443 0.206943 0.916060 0.035 Uiso 1 1 calc R . . . .
C13 C 0.4423(2) 0.7189(2) 0.81413(14) 0.0292(3) Uani 1 1 d . . . . .
H13 H 0.512235 0.778973 0.764645 0.035 Uiso 1 1 calc R . . . .
C14 C 0.3682(3) 0.8025(2) 0.88232(15) 0.0356(4) Uani 1 1 d . . . . .
H14 H 0.388384 0.919704 0.879472 0.043 Uiso 1 1 calc R . . . .
C15 C 0.2647(3) 0.7160(3) 0.95479(16) 0.0381(4) Uani 1 1 d . . . . .
H15 H 0.217377 0.775349 1.002822 0.046 Uiso 1 1 calc R . . . .
C16 C 0.2310(2) 0.5432(2) 0.95666(14) 0.0334(4) Uani 1 1 d . . . . .
H16 H 0.157645 0.482533 1.004591 0.040 Uiso 1 1 calc R . . . .
C17 C 0.2335(2) -0.0740(2) 0.39351(14) 0.0274(3) Uani 1 1 d . . . . .
H17A H 0.116474 -0.066369 0.393131 0.033 Uiso 1 1 calc R . . . .
H17B H 0.244612 -0.146813 0.446707 0.033 Uiso 1 1 calc R . . . .
C18 C 0.2267(3) -0.1606(2) 0.27336(15) 0.0340(4) Uani 1 1 d . . . . .
H18A H 0.123656 -0.286140 0.248048 0.051 Uiso 1 1 calc GR . . . .
H18B H 0.347125 -0.158739 0.273656 0.051 Uiso 1 1 calc GR . . . .
H18C H 0.205048 -0.093136 0.220230 0.051 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'
Cl Cl 0.1484 0.1585 '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 C12 113.41(11) . . ?
C7 O2 C17 116.48(11) . . ?
C7 N1 C8 116.52(12) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.04(15) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.89(14) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.15(14) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 Cl1 116.36(12) . . ?
C3 C4 C5 122.57(14) . . ?
C5 C4 Cl1 120.83(11) . . ?
C4 C5 C6 115.23(13) . . ?
C4 C5 C9 126.80(14) . . ?
C6 C5 C9 117.90(13) . . ?
C1 C6 C5 121.64(13) . . ?
C1 C6 C7 121.06(14) . . ?
C5 C6 C7 117.30(12) . . ?
O2 C7 C6 115.84(12) . . ?
N1 C7 O2 119.87(13) . . ?
N1 C7 C6 124.25(14) . . ?
O1 C8 C9 121.61(13) . . ?
N1 C8 O1 111.81(12) . . ?
N1 C8 C9 126.45(13) . . ?
C5 C9 C10 127.74(13) . . ?
C8 C9 C5 115.71(13) . . ?
C8 C9 C10 115.25(12) . . ?
C11 C10 C9 116.91(13) . . ?
C13 C10 C9 123.82(13) . . ?
C13 C10 C11 118.42(14) . . ?
C10 C11 C12 115.15(14) . . ?
C16 C11 C10 120.89(15) . . ?
C16 C11 C12 123.89(14) . . ?
O1 C12 C11 109.35(12) . . ?
O1 C12 H12A 109.8 . . ?
O1 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C10 C13 H13 119.9 . . ?
C14 C13 C10 120.26(15) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.58(16) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.73(16) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.05(15) . . ?
C15 C16 H16 120.0 . . ?
O2 C17 H17A 110.2 . . ?
O2 C17 H17B 110.2 . . ?
O2 C17 C18 107.51(12) . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 H17A 110.2 . . ?
C18 C17 H17B 110.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
Cl1 C4 1.7446(16) . ?
O1 C8 1.3597(16) . ?
O1 C12 1.4475(18) . ?
O2 C7 1.3423(17) . ?
O2 C17 1.4511(18) . ?
N1 C7 1.3067(18) . ?
N1 C8 1.3475(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.370(2) . ?
C1 C6 1.4094(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(2) . ?
C4 C5 1.421(2) . ?
C5 C6 1.421(2) . ?
C5 C9 1.4388(19) . ?
C6 C7 1.435(2) . ?
C8 C9 1.385(2) . ?
C9 C10 1.475(2) . ?
C10 C11 1.403(2) . ?
C10 C13 1.402(2) . ?
C11 C12 1.496(2) . ?
C11 C16 1.388(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.506(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
