#------------------------------------------------------------------------------
#$Date: 2018-03-15 18:33:54 +0200 (Thu, 15 Mar 2018) $
#$Revision: 206958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/84/7228469.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_7228469
loop_
_publ_author_name
'Zhang, Zhenhui'
'Liu, Kunkun'
'Chen, Xun'
'Su, Shi-Jian'
'Deng, Yuanfu'
'Zeng, Wei'
_publ_section_title
;
 Rhodium(iii)-catalyzed indole-directed carbenoid aryl C--H
 insertion/cyclization: access to 1,2-benzocarbazoles
;
_journal_issue                   49
_journal_name_full               'RSC Adv.'
_journal_page_first              30554
_journal_paper_doi               10.1039/C7RA04889K
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-10-26 deposited with the CCDC.
2017-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.489(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3910(4)
_cell_length_b                   17.2188(6)
_cell_length_c                   8.7009(3)
_cell_measurement_reflns_used    2438
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.79
_cell_measurement_theta_min      6.71
_cell_volume                     1539.71(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  bruker
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5497
_diffrn_reflns_theta_full        62.79
_diffrn_reflns_theta_max         62.79
_diffrn_reflns_theta_min         6.71
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2095
_reflns_number_total             2438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra04889k2.cif
_cod_data_source_block           zzh-1-2b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

2018-03-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C80 H68 N4 O8'
_cod_original_formula_weight         1213.38
_cod_original_formula_units_Z            1
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7228469
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.83904(12) 0.49177(7) 0.75296(13) 0.0483(3) Uani 1 1 d .
H3A H 0.8888 0.4999 0.8395 0.058 Uiso 1 1 calc R
O1 O 0.90243(11) 0.57155(7) 0.06338(11) 0.0696(4) Uani 1 1 d .
O2 O 0.77211(10) 0.66855(6) 0.11022(11) 0.0567(3) Uani 1 1 d .
C1 C 0.84769(12) 0.52891(7) 0.61584(14) 0.0413(3) Uani 1 1 d .
C2 C 0.75024(12) 0.50157(8) 0.50057(15) 0.0442(3) Uani 1 1 d .
C3 C 0.57223(16) 0.39577(10) 0.5259(2) 0.0654(4) Uani 1 1 d .
H21 H 0.5270(19) 0.3983(10) 0.417(2) 0.073(5) Uiso 1 1 d .
C4 C 0.53270(19) 0.34393(12) 0.6299(3) 0.0803(6) Uani 1 1 d .
H23 H 0.456(2) 0.3114(12) 0.593(2) 0.084(6) Uiso 1 1 d .
C5 C 0.5951(2) 0.33952(11) 0.7823(3) 0.0782(5) Uani 1 1 d .
H22 H 0.5646(19) 0.3041(12) 0.858(2) 0.082(5) Uiso 1 1 d .
C6 C 0.69817(18) 0.38714(10) 0.8354(2) 0.0651(5) Uani 1 1 d .
H15 H 0.7420(16) 0.3858(9) 0.946(2) 0.063(4) Uiso 1 1 d .
C7 C 0.73809(14) 0.43942(8) 0.73036(17) 0.0500(4) Uani 1 1 d .
C8 C 0.67814(13) 0.44439(8) 0.57494(17) 0.0491(4) Uani 1 1 d .
C9 C 0.93997(13) 0.58582(7) 0.58762(15) 0.0423(3) Uani 1 1 d .
C10 C 1.03604(13) 0.61604(9) 0.70365(16) 0.0495(4) Uani 1 1 d .
H13 H 1.0400(15) 0.5974(9) 0.813(2) 0.057(4) Uiso 1 1 d .
C11 C 1.12223(15) 0.66988(9) 0.66690(18) 0.0561(4) Uani 1 1 d .
H18 H 1.1923(16) 0.6891(9) 0.7520(18) 0.060(4) Uiso 1 1 d .
C12 C 1.11742(15) 0.69551(9) 0.51440(18) 0.0564(4) Uani 1 1 d .
H17 H 1.1820(19) 0.7329(11) 0.488(2) 0.074(5) Uiso 1 1 d .
C13 C 1.02484(14) 0.66746(8) 0.39949(18) 0.0500(4) Uani 1 1 d .
H9 H 1.0248(14) 0.6858(9) 0.2933(19) 0.055(4) Uiso 1 1 d .
C14 C 0.93334(12) 0.61182(7) 0.43186(14) 0.0416(3) Uani 1 1 d .
C15 C 0.83566(13) 0.58090(7) 0.31375(15) 0.0440(3) Uani 1 1 d .
C16 C 0.74404(12) 0.52794(8) 0.34505(15) 0.0457(4) Uani 1 1 d .
C17 C 0.64230(17) 0.49644(11) 0.2207(2) 0.0605(4) Uani 1 1 d .
H19A H 0.6443(19) 0.5166(12) 0.118(3) 0.090(6) Uiso 1 1 d .
H19B H 0.556(2) 0.5035(13) 0.244(2) 0.096(7) Uiso 1 1 d .
H19C H 0.650(2) 0.4403(13) 0.212(2) 0.086(6) Uiso 1 1 d .
C18 C 0.84099(13) 0.60499(8) 0.15003(16) 0.0472(4) Uani 1 1 d .
C19 C 0.77015(18) 0.69785(11) -0.0485(2) 0.0650(4) Uani 1 1 d .
H20A H 0.8557(19) 0.6872(10) -0.079(2) 0.075(5) Uiso 1 1 d .
H20B H 0.7534(19) 0.7572(12) -0.031(2) 0.083(6) Uiso 1 1 d .
C20 C 0.6632(2) 0.66143(12) -0.1562(2) 0.0748(5) Uani 1 1 d .
H16A H 0.579(2) 0.6678(14) -0.120(3) 0.102(7) Uiso 1 1 d .
H16B H 0.682(2) 0.6037(14) -0.166(3) 0.100(7) Uiso 1 1 d .
H16C H 0.654(2) 0.6855(13) -0.262(3) 0.102(7) Uiso 1 1 d .
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C7 109.18(11)
C18 O2 C19 117.50(12)
N1 C1 C2 109.54(12)
N1 C1 C9 127.39(11)
C2 C1 C9 123.06(12)
C1 C2 C16 120.16(12)
C1 C2 C8 106.05(12)
C16 C2 C8 133.66(13)
C4 C3 C8 119.06(19)
C3 C4 C5 121.34(19)
C6 C5 C4 121.27(17)
C5 C6 C7 117.35(18)
N1 C7 C6 128.78(15)
N1 C7 C8 108.55(12)
C6 C7 C8 122.65(15)
C3 C8 C7 118.31(14)
C3 C8 C2 135.01(15)
C7 C8 C2 106.66(12)
C10 C9 C1 123.81(12)
C10 C9 C14 119.78(13)
C1 C9 C14 116.41(11)
C11 C10 C9 120.30(14)
C10 C11 C12 120.54(14)
C13 C12 C11 120.44(15)
C12 C13 C14 121.11(14)
C13 C14 C9 117.83(12)
C13 C14 C15 122.43(12)
C9 C14 C15 119.74(12)
C16 C15 C14 122.77(12)
C16 C15 C18 119.86(12)
C14 C15 C18 117.27(12)
C15 C16 C2 117.76(12)
C15 C16 C17 122.20(13)
C2 C16 C17 120.02(13)
O1 C18 O2 123.16(13)
O1 C18 C15 124.23(12)
O2 C18 C15 112.60(11)
O2 C19 C20 110.75(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3683(17)
N1 C7 1.3751(18)
O1 C18 1.2040(17)
O2 C18 1.3255(16)
O2 C19 1.4672(19)
C1 C2 1.3975(18)
C1 C9 1.4176(19)
C2 C16 1.4197(19)
C2 C8 1.447(2)
C3 C4 1.376(3)
C3 C8 1.398(2)
C4 C5 1.390(3)
C5 C6 1.373(3)
C6 C7 1.389(2)
C7 C8 1.405(2)
C9 C10 1.4103(19)
C9 C14 1.4192(19)
C10 C11 1.360(2)
C11 C12 1.392(2)
C12 C13 1.369(2)
C13 C14 1.407(2)
C14 C15 1.4359(18)
C15 C16 1.374(2)
C15 C18 1.492(2)
C16 C17 1.498(2)
C19 C20 1.483(3)
