Rhodium-catalyzed C-H activation of 3-(indolin-1-yl)-3-oxopropanenitriles with diazo compounds and tandem cyclization leading to hydrogenated azepino[3,2,1-hi]indoles.
Zhou, Tao; Li, Bin; Wang, Baiquan; Chemical communications (Cambridge, England) 52 (2016) 14117–14120; doi:10.1039/c6cc07758g

data_7125236
_publ_section_title
;
 Rhodium-catalyzed C-H activation of 3-(indolin-1-yl)-3-oxopropanenitriles
 with diazo compounds and tandem cyclization leading to hydrogenated
 azepino[3,2,1-hi]indoles.
;
_journal_issue                   98
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14117
_journal_page_last               14120
_journal_paper_doi               10.1039/c6cc07758g
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_audit_update_record
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2016-08-11 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                79.305(11)
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_cell_angle_gamma                83.084(12)
_cell_formula_units_Z            2
_cell_length_a                   9.2814(19)
_cell_length_b                   10.2730(19)
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_cell_measurement_temperature    113
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_computing_cell_refinement
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CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
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CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
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CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
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_diffrn_ambient_temperature      113
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_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9829
	          2theta: -15.0831
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9829
	          2theta: -15.0831
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9829
	          2theta: -15.0831
;
_diffrn_measurement_device
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AFC10: Fixed Chi 2 circle
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_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
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_diffrn_orient_matrix_UB_11      -0.102785
_diffrn_orient_matrix_UB_12      0.027295
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_diffrn_orient_matrix_UB_33      0.057315
_diffrn_radiation_monochromator  Confocal
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.990
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14022
_diffrn_reflns_point_group_measured_fraction_full 0.990
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         3.076
_diffrn_source                   'Rotating Anode'
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_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             384
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
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_refine_diff_density_max         0.639
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0512
_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/[\s^2^(Fo^2^)+(0.0531P)^2^+0.9818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4059
_reflns_number_total             4895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07758g2.cif
_cod_data_source_block           m20160126c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7125236
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              79501
_shelx_fab_checksum              20930
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'