# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#===============================================================================
data_global
#===============================================================================
# 1. SUBMISSION DETAILS

_audit_creation_method           'APEX2 v2012.12-0'

_publ_requested_journal          'New Journal of Chemistry'

_publ_contact_author_name        'Jonathon S. Lindsey'
_publ_contact_author_address     
;
Department of Chemistry
NC State University
2620 Yarbrough Drive
Box 8204
Raleigh, NC 27695
;
_publ_contact_author_email       jlindsey@ncsu.edu
_publ_contact_author_fax         919-515-2830
_publ_contact_author_phone       919-515-6406



#===============================================================================

# 2. PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#===============================================================================

# 3. TITLE AND AUTHOR LIST
_publ_section_title              
;
Regioselective beta-Pyrrolic Electrophilic Substitution of Hydrodipyrrin-
Dialkylboron Complexes Facilitates Access to Synthetic Models for Chlorophyll f
;
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address

'Mengran Liu'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Marcin Ptaszek'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Olga Mass'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Daniel F. Minkler'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Roger D. Sommer'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jayeeta Bhaumik'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jonathan S. Lindsey'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;


#===============================================================================
# 4. TEXT
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;

data_I
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic        
;
 ?  #Insert the chemical name here.
;
_chemical_formula_analytical     ?
_chemical_formula_moiety         'C20 H35 B N2 '
_chemical_formula_structural     ?
_chemical_formula_sum            'C20 H35 B N2 '
_chemical_formula_weight         314.32
_chemical_compound_source        ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C ? .003 .002 'International Tables Vol. IV Table 2.2B'
H ? .000 .000 'International Tables Vol. IV Table 2.2B'
B ? .001 .001 'International Tables Vol. IV Table 2.2B'
N ? .006 .003 'International Tables Vol. IV Table 2.2B'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
3 1/2-x,1/2+y,1/2-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   15.8194(3)
_cell_length_b                   7.93900(10)
_cell_length_c                   16.6596(3)
_cell_angle_alpha                90.0
_cell_angle_beta                 110.7227(8)
_cell_angle_gamma                90.0
_cell_volume                     1956.92(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9052
_cell_measurement_temperature    110
_cell_measurement_theta_max      22.191
_cell_measurement_theta_min      2.208
_cell_special_details            
;
 ?  #Insert any comments here.
;
_exptl_absorpt_coefficient_mu    .06
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.922504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0410 before and 0.0352 after correction.
The Ratio of minimum to maximum transmission is 0.9225.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'pale greenish yellow'
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             696.32
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_crystal_size_rad          ?
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details           
;
 ?  #Insert any special details here.
;
_diffrn_reflns_av_R_equivalents  .031
_diffrn_reflns_av_unetI/netI     ?
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            110726
_diffrn_reflns_reduction_process ?
_diffrn_reflns_theta_max         26.66
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_full        26.66
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_ambient_temperature      110.0
_diffrn_measurement_device       'Bruker-Nonius X8 Apex2'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_source                   'xray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_number_observed          2997
_reflns_number_total             4114
_reflns_observed_criterion       'Inet > 2.5\s(Inet)'
_computing_cell_refinement       Apex2
_computing_data_collection       Apex2
_computing_data_reduction        SAINT+
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    SIR92
_refine_diff_density_max         .47
_refine_diff_density_min         -.24
_refine_ls_extinction_coef       0.5(4)
_refine_ls_extinction_method     Larson
_refine_ls_goodness_of_fit_all   ?
_refine_ls_goodness_of_fit_obs   2.80
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    ?
_refine_ls_number_parameters     349
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     ?
_refine_ls_R_factor_all          .074
_refine_ls_R_factor_obs          .052
_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/esd_max         .000
_refine_ls_shift/esd_mean        ?
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/(σ²(F)+ .0005F²) '
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .157
_refine_ls_wR_factor_obs         .079
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details          
;
 ?  #Insert any special details here.
;
#===============================================================================
# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
_atom_site_occupancy
B1 .58015(14) .2350(3) .88649(13) .0269(12) Uani ? . B .
N1 .55036(9) .09394(19) .81041(9) .0237(9) Uani ? . N .
N2 .62672(10) .37833(19) .85210(10) .0274(9) Uani ? . N .
C1 .51326(11) -.0512(2) .81021(11) .0237(10) Uani ? . C .
C2 .50303(15) -.1530(3) .73188(12) .0276(11) Uani ? . C .
C3 .51597(12) -.0237(2) .66852(11) .0282(11) Uani ? . C .
C4 .57472(14) .1092(2) .73102(12) .0300(12) Uani ? . C .
C5 .56833(15) .2876(3) .70084(13) .0355(13) Uani ? . C .
C6 .62607(12) .4005(2) .77034(12) .0287(11) Uani ? . C .
C7 .67818(13) .5383(3) .76754(15) .0355(14) Uani ? . C .
C8 .71168(14) .6048(3) .85127(15) .0409(14) Uani ? . C .
C9 .67986(14) .5053(3) .90123(15) .0384(13) Uani ? . C .
C10 .48578(17) -.1219(3) .87942(14) .0348(13) Uani ? . C .
C11 .42341(14) .0430(3) .61177(14) .0349(13) Uani ? . C .
C12 .56692(15) -.0931(3) .61349(14) .0319(12) Uani ? . C .
C13 .49148(13) .3087(3) .90064(12) .0291(11) Uani ? . C .
C14 .42031(13) .3907(3) .82375(12) .0261(11) Uani ? . C .
C15 .33861(13) .4608(3) .84035(13) .0312(12) Uani ? . C .
C16 .26950(16) .5412(4) .76203(17) .0441(15) Uani ? . C .
C17 .65449(13) .1528(3) .97109(12) .0285(12) Uani ? . C .
C18 .73988(13) .0859(3) .96017(13) .0287(11) Uani ? . C .
C19 .80918(13) .0122(3) 1.04105(13) .0312(12) Uani ? . C .
C20 .89557(15) -.0429(3) 1.02869(15) .0369(13) Uani ? . C .
H2a .5479(14) -.239(3) .7492(12) .039(6) Uiso ? . H .
H2b .4449(15) -.211(3) .7127(12) .037(5) Uiso ? . H .
H4 .6484(14) .069(3) .7516(12) .038(5) Uiso ? . H .
H5a .497(2) .318(4) .6807(16) .078(8) Uiso ? . H .
H5b .5906(12) .300(3) .6502(12) .034(5) Uiso ? . H .
H7 .6889(13) .571(3) .7167(13) .037(6) Uiso ? . H .
H8 .7493(13) .705(3) .8722(12) .038(5) Uiso ? . H .
H9 .6881(14) .515(3) .9643(15) .047(6) Uiso ? . H .
H10a .4967(15) -.046(3) .9276(15) .052(7) Uiso ? . H .
H10b .422(2) -.162(4) .8576(17) .085(9) Uiso ? . H .
H10c .5227(16) -.217(4) .9025(15) .061(8) Uiso ? . H .
H11a .3912(13) .088(2) .6455(12) .031(5) Uiso ? . H .
H11b .4287(12) .129(3) .5697(12) .030(5) Uiso ? . H .
H11c .3808(15) -.049(3) .5731(13) .044(6) Uiso ? . H .
H12a .6285(17) -.137(3) .6469(14) .047(6) Uiso ? . H .
H12b .5287(13) -.181(3) .5714(13) .041(6) Uiso ? . H .
H12c .5783(12) -.003(3) .5770(12) .029(5) Uiso ? . H .
H13a .5099(13) .397(3) .9449(13) .037(5) Uiso ? . H .
H13b .4616(12) .219(3) .9228(12) .032(5) Uiso ? . H .
H14a .4438(12) .489(3) .7991(11) .032(5) Uiso ? . H .
H14b .3968(13) .314(3) .7746(13) .037(5) Uiso ? . H .
H15a .3586(12) .542(2) .8854(12) .024(5) Uiso ? . H .
H15b .3106(11) .367(2) .8655(10) .017(4) Uiso ? . H .
H16a .2169(14) .589(3) .7724(12) .035(5) Uiso ? . H .
H16b .3023(15) .644(3) .7449(14) .053(7) Uiso ? . H .
H16c .2463(15) .465(3) .7155(15) .047(7) Uiso ? . H .
H17a .6243(12) .059(3) .9925(12) .032(5) Uiso ? . H .
H17b .6701(13) .231(3) 1.0184(14) .035(5) Uiso ? . H .
H18a .7257(13) .009(3) .9177(13) .033(5) Uiso ? . H .
H18b .7709(11) .184(3) .9375(10) .025(5) Uiso ? . H .
H19a .8245(14) .091(3) 1.0880(13) .036(6) Uiso ? . H .
H19b .7839(12) -.096(3) 1.0617(11) .032(5) Uiso ? . H .
H20a .9387(13) -.087(3) 1.0859(13) .034(5) Uiso ? . H .
H20b .8850(14) -.141(3) .9866(14) .050(6) Uiso ? . H .
H20c .9220(18) .047(4) 1.0061(16) .070(8) Uiso ? . H .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.631(3) ? ? ?
B1 N2 1.570(3) ? ? ?
B1 C13 1.612(3) ? ? ?
B1 C17 1.619(3) ? ? ?
N1 C1 1.293(2) ? ? ?
N1 C4 1.508(2) ? ? ?
N2 C6 1.370(2) ? ? ?
N2 C9 1.380(3) ? ? ?
C1 C2 1.494(3) ? ? ?
C1 C10 1.479(3) ? ? ?
C2 C3 1.537(3) ? ? ?
C2 H2a .95(2) ? ? ?
C2 H2b .98(2) ? ? ?
C3 C4 1.541(3) ? ? ?
C3 C11 1.529(3) ? ? ?
C3 C12 1.522(3) ? ? ?
C4 C5 1.495(3) ? ? ?
C4 H4 1.14(2) ? ? ?
C5 C6 1.493(3) ? ? ?
C5 H5a 1.09(3) ? ? ?
C5 H5b 1.03(2) ? ? ?
C6 C7 1.381(3) ? ? ?
C7 C8 1.408(3) ? ? ?
C7 H7 .96(2) ? ? ?
C8 C9 1.366(3) ? ? ?
C8 H8 .98(2) ? ? ?
C9 H9 1.02(2) ? ? ?
C10 H10a .97(3) ? ? ?
C10 H10b 1.00(3) ? ? ?
C10 H10c .95(3) ? ? ?
C11 H11a .95(2) ? ? ?
C11 H11b 1.00(2) ? ? ?
C11 H11c 1.04(2) ? ? ?
C12 H12a 1.00(3) ? ? ?
C12 H12b 1.02(2) ? ? ?
C12 H12c 1.00(2) ? ? ?
C13 C14 1.520(3) ? ? ?
C13 H13a .98(2) ? ? ?
C13 H13b 1.00(2) ? ? ?
C14 C15 1.520(3) ? ? ?
C14 H14a 1.01(2) ? ? ?
C14 H14b .98(2) ? ? ?
C15 C16 1.515(3) ? ? ?
C15 H15a .96(2) ? ? ?
C15 H15b 1.026(19) ? ? ?
C16 H16a .98(2) ? ? ?
C16 H16b 1.06(3) ? ? ?
C16 H16c .95(3) ? ? ?
C17 C18 1.521(3) ? ? ?
C17 H17a 1.01(2) ? ? ?
C17 H17b .97(2) ? ? ?
C18 C19 1.521(3) ? ? ?
C18 H18a .90(2) ? ? ?
C18 H18b 1.06(2) ? ? ?
C19 C20 1.517(3) ? ? ?
C19 H19a .96(2) ? ? ?
C19 H19b 1.05(2) ? ? ?
C20 H20a 1.02(2) ? ? ?
C20 H20b 1.02(3) ? ? ?
C20 H20c .97(3) ? ? ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 B1 N2 104.95(14) ? ? ? ?
N1 B1 C13 109.62(15) ? ? ? ?
N1 B1 C17 108.71(15) ? ? ? ?
N2 B1 C13 109.57(16) ? ? ? ?
N2 B1 C17 108.65(15) ? ? ? ?
C13 B1 C17 114.87(15) ? ? ? ?
B1 N1 C1 128.32(15) ? ? ? ?
B1 N1 C4 122.24(14) ? ? ? ?
C1 N1 C4 109.03(14) ? ? ? ?
B1 N2 C6 128.06(15) ? ? ? ?
B1 N2 C9 125.37(16) ? ? ? ?
C6 N2 C9 106.53(17) ? ? ? ?
N1 C1 C2 113.15(15) ? ? ? ?
N1 C1 C10 126.48(17) ? ? ? ?
C2 C1 C10 120.31(17) ? ? ? ?
C1 C2 C3 103.81(16) ? ? ? ?
C1 C2 H2a 106.5(12) ? ? ? ?
C1 C2 H2b 109.8(12) ? ? ? ?
C3 C2 H2a 114.9(12) ? ? ? ?
C3 C2 H2b 115.4(11) ? ? ? ?
H2a C2 H2b 106.1(16) ? ? ? ?
C2 C3 C4 100.85(14) ? ? ? ?
C2 C3 C11 108.96(17) ? ? ? ?
C2 C3 C12 113.53(17) ? ? ? ?
C4 C3 C11 113.39(17) ? ? ? ?
C4 C3 C12 109.48(16) ? ? ? ?
C11 C3 C12 110.39(16) ? ? ? ?
N1 C4 C3 104.93(15) ? ? ? ?
N1 C4 C5 111.30(16) ? ? ? ?
N1 C4 H4 105.4(9) ? ? ? ?
C3 C4 C5 117.94(16) ? ? ? ?
C3 C4 H4 108.5(10) ? ? ? ?
C5 C4 H4 108.1(10) ? ? ? ?
C4 C5 C6 110.97(17) ? ? ? ?
C4 C5 H5a 104.6(15) ? ? ? ?
C4 C5 H5b 111.3(11) ? ? ? ?
C6 C5 H5a 113.1(14) ? ? ? ?
C6 C5 H5b 106.7(10) ? ? ? ?
H5a C5 H5b 110.3(17) ? ? ? ?
N2 C6 C5 118.77(16) ? ? ? ?
N2 C6 C7 109.93(17) ? ? ? ?
C5 C6 C7 131.16(19) ? ? ? ?
C6 C7 C8 106.47(20) ? ? ? ?
C6 C7 H7 122.8(12) ? ? ? ?
C8 C7 H7 130.7(12) ? ? ? ?
C7 C8 C9 107.23(19) ? ? ? ?
C7 C8 H8 128.6(11) ? ? ? ?
C9 C8 H8 124.1(11) ? ? ? ?
N2 C9 C8 109.83(20) ? ? ? ?
N2 C9 H9 120.0(12) ? ? ? ?
C8 C9 H9 130.1(12) ? ? ? ?
C1 C10 H10a 113.1(14) ? ? ? ?
C1 C10 H10b 112.3(15) ? ? ? ?
C1 C10 H10c 108.0(14) ? ? ? ?
H10a C10 H10b 111(2) ? ? ? ?
H10a C10 H10c 105.0(19) ? ? ? ?
H10b C10 H10c 106(2) ? ? ? ?
C3 C11 H11a 111.1(11) ? ? ? ?
C3 C11 H11b 111.6(10) ? ? ? ?
C3 C11 H11c 114.1(11) ? ? ? ?
H11a C11 H11b 110.5(16) ? ? ? ?
H11a C11 H11c 105.4(16) ? ? ? ?
H11b C11 H11c 103.8(15) ? ? ? ?
C3 C12 H12a 114.2(12) ? ? ? ?
C3 C12 H12b 110.5(11) ? ? ? ?
C3 C12 H12c 110.9(11) ? ? ? ?
H12a C12 H12b 111.7(16) ? ? ? ?
H12a C12 H12c 103.8(16) ? ? ? ?
H12b C12 H12c 105.2(15) ? ? ? ?
B1 C13 C14 117.09(16) ? ? ? ?
B1 C13 H13a 109.0(11) ? ? ? ?
B1 C13 H13b 110.1(10) ? ? ? ?
C14 C13 H13a 105.1(11) ? ? ? ?
C14 C13 H13b 108.2(10) ? ? ? ?
H13a C13 H13b 106.7(15) ? ? ? ?
C13 C14 C15 115.30(16) ? ? ? ?
C13 C14 H14a 113.8(10) ? ? ? ?
C13 C14 H14b 112.8(11) ? ? ? ?
C15 C14 H14a 104.3(11) ? ? ? ?
C15 C14 H14b 106.4(11) ? ? ? ?
H14a C14 H14b 103.0(15) ? ? ? ?
C14 C15 C16 113.49(18) ? ? ? ?
C14 C15 H15a 108.9(11) ? ? ? ?
C14 C15 H15b 109.2(9) ? ? ? ?
C16 C15 H15a 109.1(11) ? ? ? ?
C16 C15 H15b 111.8(9) ? ? ? ?
H15a C15 H15b 103.8(14) ? ? ? ?
C15 C16 H16a 114.1(11) ? ? ? ?
C15 C16 H16b 106.5(12) ? ? ? ?
C15 C16 H16c 112.9(14) ? ? ? ?
H16a C16 H16b 106.0(17) ? ? ? ?
H16a C16 H16c 106.4(17) ? ? ? ?
H16b C16 H16c 110.8(18) ? ? ? ?
B1 C17 C18 116.03(16) ? ? ? ?
B1 C17 H17a 108.3(10) ? ? ? ?
B1 C17 H17b 110.2(11) ? ? ? ?
C18 C17 H17a 109.6(10) ? ? ? ?
C18 C17 H17b 110.0(11) ? ? ? ?
H17a C17 H17b 101.8(15) ? ? ? ?
C17 C18 C19 114.86(17) ? ? ? ?
C17 C18 H18a 110.2(12) ? ? ? ?
C17 C18 H18b 109.2(9) ? ? ? ?
C19 C18 H18a 109.6(12) ? ? ? ?
C19 C18 H18b 108.6(9) ? ? ? ?
H18a C18 H18b 103.8(15) ? ? ? ?
C18 C19 C20 113.09(17) ? ? ? ?
C18 C19 H19a 111.5(12) ? ? ? ?
C18 C19 H19b 111.3(10) ? ? ? ?
C20 C19 H19a 108.5(12) ? ? ? ?
C20 C19 H19b 105.9(10) ? ? ? ?
H19a C19 H19b 106.2(15) ? ? ? ?
C19 C20 H20a 108.0(11) ? ? ? ?
C19 C20 H20b 112.2(12) ? ? ? ?
C19 C20 H20c 111.8(15) ? ? ? ?
H20a C20 H20b 106.1(16) ? ? ? ?
H20a C20 H20c 112.2(19) ? ? ? ?
H20b C20 H20c 106.5(19) ? ? ? ?


_database_code_depnum_ccdc_archive 'CCDC 974409'
#===============================================================================
data_global
#===============================================================================
# 1. SUBMISSION DETAILS

_audit_creation_method           'APEX2 v2012.12-0'

_publ_requested_journal          'New Journal of Chemistry'

_publ_contact_author_name        'Jonathon S. Lindsey'
_publ_contact_author_address     
;
Department of Chemistry
NC State University
2620 Yarbrough Drive
Box 8204
Raleigh, NC 27695
;
_publ_contact_author_email       jlindsey@ncsu.edu
_publ_contact_author_fax         919-515-2830
_publ_contact_author_phone       919-515-6406



#===============================================================================

# 2. PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#===============================================================================

# 3. TITLE AND AUTHOR LIST
_publ_section_title              
;
Regioselective beta-Pyrrolic Electrophilic Substitution of Hydrodipyrrin-
Dialkylboron Complexes Facilitates Access to Synthetic Models for Chlorophyll f
;
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address

'Mengran Liu'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Marcin Ptaszek'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Olga Mass'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Daniel F. Minkler'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Roger D. Sommer'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jayeeta Bhaumik'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jonathan S. Lindsey'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;


#===============================================================================
# 4. TEXT
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;

#===============================================================================

data_I
_chemical_name_systematic        ?
_chemical_name_common            Br8
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H34 B Br N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         393.21

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8715(3)
_cell_length_b                   26.3874(12)
_cell_length_c                   9.8079(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.588(2)
_cell_angle_gamma                90
_cell_volume                     2070.80(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    503
_cell_measurement_theta_min      2.4267
_cell_measurement_theta_max      25.9732
_cell_measurement_temperature    110.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    1.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.69

_exptl_special_details           
;
;

_diffrn_ambient_temperature      110.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            29325
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             5130
_reflns_number_gt                4271
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1343
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_number_reflns         5130
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.0218P)²+7.0976P]
where P=(Fo²+2Fc²)/3
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.076
_refine_diff_density_min         -1.507
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2013.6-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.69334(5) 0.68250(2) 0.39043(5) 0.03953(14) Uani d . . . 1 . .
N N1 0.1702(3) 0.61911(10) 0.6696(3) 0.0201(6) Uani d . . . 1 . .
N N2 0.3789(4) 0.63205(11) 0.5605(3) 0.0212(6) Uani d . . . 1 . .
B B1 0.2489(5) 0.59246(15) 0.5640(5) 0.0247(8) Uani d . . . 1 . .
C C1 0.0508(4) 0.60319(13) 0.6988(4) 0.0224(7) Uani d . . . 1 . .
C C2 0.0047(5) 0.63963(15) 0.7910(4) 0.0288(8) Uani d . . . 1 . .
H H2A -0.0073 0.622 0.8749 0.035 Uiso calc U . R 1 . .
H H2B -0.1015 0.6571 0.7278 0.035 Uiso calc U . R 1 . .
C C3 0.1501(5) 0.67729(14) 0.8519(4) 0.0284(8) Uani d . . . 1 . .
C C4 0.2182(5) 0.67179(14) 0.7305(4) 0.0294(8) Uani d . . . 1 . .
H H4 0.1547 0.696 0.6467 0.035 Uiso calc U . R 1 . .
C C5 0.3985(5) 0.68192(16) 0.7805(4) 0.0329(8) Uani d . . . 1 . .
H H5A 0.465 0.6595 0.8666 0.039 Uiso calc U . R 1 . .
H H5B 0.4236 0.7175 0.815 0.039 Uiso calc U . R 1 . .
C C6 0.4460(5) 0.67266(14) 0.6522(4) 0.0284(8) Uani d . . . 1 . .
C C7 0.5582(5) 0.69716(15) 0.6133(5) 0.0328(8) Uani d . . . 1 . .
H H7 0.6214 0.7267 0.6584 0.039 Uiso calc U . R 1 . .
C C8 0.5590(4) 0.66889(15) 0.4916(4) 0.0273(8) Uani d . . . 1 . .
C C9 0.4514(5) 0.62989(15) 0.4626(4) 0.0312(8) Uani d . . . 1 . .
H H9 0.4295 0.605 0.3865 0.037 Uiso calc U . R 1 . .
C C10 -0.0445(5) 0.55543(16) 0.6463(5) 0.0356(9) Uani d . . . 1 . .
H H10A -0.1586 0.5632 0.572 0.053 Uiso calc U . R 1 . .
H H10B -0.0481 0.5377 0.7326 0.053 Uiso calc U . R 1 . .
H H10C 0.0101 0.5339 0.5996 0.053 Uiso calc U . R 1 . .
C C11 0.2758(5) 0.66172(17) 1.0094(4) 0.0378(9) Uani d . . . 1 . .
H H11A 0.2209 0.6611 1.0773 0.057 Uiso calc U . R 1 . .
H H11B 0.3682 0.6861 1.0471 0.057 Uiso calc U . R 1 . .
H H11C 0.3193 0.6279 1.0052 0.057 Uiso calc U . R 1 . .
C C12 0.0937(6) 0.73182(16) 0.8523(5) 0.0423(10) Uani d . . . 1 . .
H H12A 0.0093 0.7408 0.7511 0.064 Uiso calc U . R 1 . .
H H12B 0.1899 0.7546 0.8811 0.064 Uiso calc U . R 1 . .
H H12C 0.0457 0.7352 0.925 0.064 Uiso calc U . R 1 . .
C C13 0.3428(5) 0.54012(14) 0.6387(4) 0.0307(8) Uani d . . . 1 . .
H H13A 0.2622 0.5185 0.6568 0.037 Uiso calc U . R 1 . .
H H13B 0.3698 0.5226 0.5628 0.037 Uiso calc U . R 1 . .
C C14 0.5004(5) 0.54263(15) 0.7837(5) 0.0373(9) Uani d . . . 1 . .
H H14A 0.4723 0.5535 0.8666 0.045 Uiso calc U . R 1 . .
H H14B 0.5762 0.5683 0.7735 0.045 Uiso calc U . R 1 . .
C C15 0.5910(6) 0.49149(17) 0.8249(6) 0.0491(12) Uani d . . . 1 . .
H H15A 0.5169 0.4664 0.8405 0.059 Uiso calc U . R 1 . .
H H15B 0.6118 0.4797 0.7387 0.059 Uiso calc U . R 1 . .
C C16 0.7537(7) 0.4929(2) 0.9634(7) 0.0617(15) Uani d . . . 1 . .
H H16A 0.8272 0.5182 0.9501 0.092 Uiso calc U . R 1 . .
H H16B 0.8068 0.4595 0.9798 0.092 Uiso calc U . R 1 . .
H H16C 0.7336 0.502 1.051 0.092 Uiso calc U . R 1 . .
C C17 0.1040(5) 0.58502(14) 0.3936(4) 0.0273(8) Uani d . . . 1 . .
H H17A 0.1508 0.5645 0.3364 0.033 Uiso calc U . R 1 . .
H H17B 0.0124 0.5651 0.3993 0.033 Uiso calc U . R 1 . .
C C18 0.0292(5) 0.63290(14) 0.3037(4) 0.0262(7) Uani d . . . 1 . .
H H18A 0.1194 0.6527 0.295 0.031 Uiso calc U . R 1 . .
H H18B -0.0174 0.6538 0.3603 0.031 Uiso calc U . R 1 . .
C C19 -0.1079(5) 0.62310(17) 0.1457(4) 0.0351(9) Uani d . . . 1 . .
H H19A -0.0626 0.601 0.0907 0.042 Uiso calc U . R 1 . .
H H19B -0.2001 0.6045 0.1547 0.042 Uiso calc U . R 1 . .
C C20 -0.1778(6) 0.67056(19) 0.0539(4) 0.0429(11) Uani d . . . 1 . .
H H20A -0.2371 0.6904 0.0999 0.064 Uiso calc U . R 1 . .
H H20B -0.2554 0.6613 -0.0495 0.064 Uiso calc U . R 1 . .
H H20C -0.0861 0.6908 0.0518 0.064 Uiso calc U . R 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C8 . 1.886(3) ?
N1 C1 . 1.282(4) ?
N1 C4 . 1.500(4) ?
N1 B1 . 1.637(4) ?
N2 C6 . 1.360(5) ?
N2 C9 . 1.369(4) ?
N2 B1 . 1.567(5) ?
B1 C13 . 1.616(6) ?
B1 C17 . 1.621(5) ?
C1 C10 . 1.481(5) ?
C1 C2 . 1.493(5) ?
C2 C3 . 1.530(5) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C11 . 1.520(5) ?
C3 C12 . 1.524(5) ?
C3 C4 . 1.557(5) ?
C4 C5 . 1.481(5) ?
C4 H4 . 1.0 ?
C5 C6 . 1.510(5) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.371(5) ?
C7 C8 . 1.410(5) ?
C7 H7 . 0.95 ?
C8 C9 . 1.348(5) ?
C9 H9 . 0.95 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.505(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.533(6) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.495(7) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 C18 . 1.519(5) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C19 . 1.523(5) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.511(6) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C4 . . 109.5(3) ?
C1 N1 B1 . . 128.3(3) ?
C4 N1 B1 . . 121.7(3) ?
C6 N2 C9 . . 107.0(3) ?
C6 N2 B1 . . 128.9(3) ?
C9 N2 B1 . . 124.1(3) ?
N2 B1 C13 . . 109.9(3) ?
N2 B1 C17 . . 108.7(3) ?
C13 B1 C17 . . 112.8(3) ?
N2 B1 N1 . . 104.3(3) ?
C13 B1 N1 . . 111.0(3) ?
C17 B1 N1 . . 109.8(3) ?
N1 C1 C10 . . 127.2(3) ?
N1 C1 C2 . . 113.2(3) ?
C10 C1 C2 . . 119.6(3) ?
C1 C2 C3 . . 104.4(3) ?
C1 C2 H2A . . 110.9 ?
C3 C2 H2A . . 110.9 ?
C1 C2 H2B . . 110.9 ?
C3 C2 H2B . . 110.9 ?
H2A C2 H2B . . 108.9 ?
C11 C3 C12 . . 110.5(3) ?
C11 C3 C2 . . 110.2(3) ?
C12 C3 C2 . . 113.1(3) ?
C11 C3 C4 . . 113.3(3) ?
C12 C3 C4 . . 109.0(3) ?
C2 C3 C4 . . 100.4(3) ?
C5 C4 N1 . . 112.3(3) ?
C5 C4 C3 . . 116.8(3) ?
N1 C4 C3 . . 104.7(3) ?
C5 C4 H4 . . 107.6 ?
N1 C4 H4 . . 107.6 ?
C3 C4 H4 . . 107.6 ?
C4 C5 C6 . . 110.2(3) ?
C4 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
C4 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
N2 C6 C7 . . 110.6(3) ?
N2 C6 C5 . . 118.6(3) ?
C7 C6 C5 . . 130.8(4) ?
C6 C7 C8 . . 104.8(3) ?
C6 C7 H7 . . 127.6 ?
C8 C7 H7 . . 127.6 ?
C9 C8 C7 . . 108.7(3) ?
C9 C8 Br1 . . 125.8(3) ?
C7 C8 Br1 . . 125.5(3) ?
C8 C9 N2 . . 109.0(3) ?
C8 C9 H9 . . 125.5 ?
N2 C9 H9 . . 125.5 ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C3 C11 H11A . . 109.5 ?
C3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C3 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C3 C12 H12A . . 109.5 ?
C3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 B1 . . 118.5(3) ?
C14 C13 H13A . . 107.7 ?
B1 C13 H13A . . 107.7 ?
C14 C13 H13B . . 107.7 ?
B1 C13 H13B . . 107.7 ?
H13A C13 H13B . . 107.1 ?
C13 C14 C15 . . 112.2(4) ?
C13 C14 H14A . . 109.2 ?
C15 C14 H14A . . 109.2 ?
C13 C14 H14B . . 109.2 ?
C15 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C16 C15 C14 . . 114.1(4) ?
C16 C15 H15A . . 108.7 ?
C14 C15 H15A . . 108.7 ?
C16 C15 H15B . . 108.7 ?
C14 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 B1 . . 116.8(3) ?
C18 C17 H17A . . 108.1 ?
B1 C17 H17A . . 108.1 ?
C18 C17 H17B . . 108.1 ?
B1 C17 H17B . . 108.1 ?
H17A C17 H17B . . 107.3 ?
C17 C18 C19 . . 113.9(3) ?
C17 C18 H18A . . 108.8 ?
C19 C18 H18A . . 108.8 ?
C17 C18 H18B . . 108.8 ?
C19 C18 H18B . . 108.8 ?
H18A C18 H18B . . 107.7 ?
C20 C19 C18 . . 114.1(3) ?
C20 C19 H19A . . 108.7 ?
C18 C19 H19A . . 108.7 ?
C20 C19 H19B . . 108.7 ?
C18 C19 H19B . . 108.7 ?
H19A C19 H19B . . 107.6 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N2 B1 C13 . . . . -103.3(4) ?
C9 N2 B1 C13 . . . . 74.0(4) ?
C6 N2 B1 C17 . . . . 132.8(4) ?
C9 N2 B1 C17 . . . . -49.9(4) ?
C6 N2 B1 N1 . . . . 15.7(5) ?
C9 N2 B1 N1 . . . . -167.0(3) ?
C1 N1 B1 N2 . . . . 175.1(3) ?
C4 N1 B1 N2 . . . . 3.8(4) ?
C1 N1 B1 C13 . . . . -66.7(5) ?
C4 N1 B1 C13 . . . . 122.0(3) ?
C1 N1 B1 C17 . . . . 58.7(4) ?
C4 N1 B1 C17 . . . . -112.5(3) ?
C4 N1 C1 C10 . . . . 173.6(4) ?
B1 N1 C1 C10 . . . . 1.5(6) ?
C4 N1 C1 C2 . . . . -3.7(4) ?
B1 N1 C1 C2 . . . . -175.8(3) ?
N1 C1 C2 C3 . . . . -14.4(4) ?
C10 C1 C2 C3 . . . . 168.0(3) ?
C1 C2 C3 C11 . . . . -95.2(3) ?
C1 C2 C3 C12 . . . . 140.6(3) ?
C1 C2 C3 C4 . . . . 24.5(4) ?
C1 N1 C4 C5 . . . . 147.7(3) ?
B1 N1 C4 C5 . . . . -39.6(4) ?
C1 N1 C4 C3 . . . . 20.0(4) ?
B1 N1 C4 C3 . . . . -167.2(3) ?
C11 C3 C4 C5 . . . . -34.1(5) ?
C12 C3 C4 C5 . . . . 89.3(4) ?
C2 C3 C4 C5 . . . . -151.6(3) ?
C11 C3 C4 N1 . . . . 90.7(4) ?
C12 C3 C4 N1 . . . . -145.8(3) ?
C2 C3 C4 N1 . . . . -26.8(4) ?
N1 C4 C5 C6 . . . . 56.5(4) ?
C3 C4 C5 C6 . . . . 177.4(3) ?
C9 N2 C6 C7 . . . . 1.1(4) ?
B1 N2 C6 C7 . . . . 178.7(3) ?
C9 N2 C6 C5 . . . . -175.3(3) ?
B1 N2 C6 C5 . . . . 2.4(6) ?
C4 C5 C6 N2 . . . . -40.3(5) ?
C4 C5 C6 C7 . . . . 144.3(4) ?
N2 C6 C7 C8 . . . . -0.7(5) ?
C5 C6 C7 C8 . . . . 175.0(4) ?
C6 C7 C8 C9 . . . . 0.1(5) ?
C6 C7 C8 Br1 . . . . -178.4(3) ?
C7 C8 C9 N2 . . . . 0.6(5) ?
Br1 C8 C9 N2 . . . . 179.0(3) ?
C6 N2 C9 C8 . . . . -1.0(4) ?
B1 N2 C9 C8 . . . . -178.8(3) ?
N2 B1 C13 C14 . . . . 47.1(4) ?
C17 B1 C13 C14 . . . . 168.6(3) ?
N1 B1 C13 C14 . . . . -67.7(4) ?
B1 C13 C14 C15 . . . . -169.8(4) ?
C13 C14 C15 C16 . . . . 176.5(4) ?
N2 B1 C17 C18 . . . . -47.5(4) ?
C13 B1 C17 C18 . . . . -169.7(3) ?
N1 B1 C17 C18 . . . . 66.0(4) ?
B1 C17 C18 C19 . . . . -179.1(3) ?
C17 C18 C19 C20 . . . . -177.7(3) ?




_database_code_depnum_ccdc_archive 'CCDC 974410'
#===============================================================================
data_global
#===============================================================================
# 1. SUBMISSION DETAILS

_audit_creation_method           'APEX2 v2012.12-0'

_publ_requested_journal          'New Journal of Chemistry'

_publ_contact_author_name        'Jonathon S. Lindsey'
_publ_contact_author_address     
;
Department of Chemistry
NC State University
2620 Yarbrough Drive
Box 8204
Raleigh, NC 27695
;
_publ_contact_author_email       jlindsey@ncsu.edu
_publ_contact_author_fax         919-515-2830
_publ_contact_author_phone       919-515-6406



#===============================================================================

# 2. PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#===============================================================================

# 3. TITLE AND AUTHOR LIST
_publ_section_title              
;
Regioselective beta-Pyrrolic Electrophilic Substitution of Hydrodipyrrin-
Dialkylboron Complexes Facilitates Access to Synthetic Models for Chlorophyll f
;
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address

'Mengran Liu'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Marcin Ptaszek'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Olga Mass'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Daniel F. Minkler'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Roger D. Sommer'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jayeeta Bhaumik'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jonathan S. Lindsey'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;


#===============================================================================
# 4. TEXT
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;
#===============================================================================
data_rds011
_audit_creation_date             2013-11-25
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2013.03.22 svn.r2654, GUI svn.r4446)
;
_publ_contact_author_address     ?
_publ_contact_author_email       ?
_publ_contact_author_phone       ?
_chemical_formula_moiety         'C21 H34 B Br1 N2 O'
_chemical_formula_sum            'C21 H34 B Br N2 O'
_chemical_formula_weight         421.24
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,z

_cell_length_a                   17.5208(3)
_cell_length_b                   16.5255(3)
_cell_length_c                   15.1765(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4394.20(14)
_cell_formula_units_Z            8
_exptl_absorpt_coefficient_mu    1.882
_exptl_crystal_density_diffrn    1.2734
_exptl_crystal_F_000             1774.3418
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.09
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            77149
_diffrn_reflns_theta_full        27.3167
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         1.69
_diffrn_measured_fraction_theta_full 0.9623
_diffrn_measured_fraction_theta_max 0.9623
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.924
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              21
_reflns_limit_k_min              -21
_reflns_limit_l_max              17
_reflns_limit_l_min              -19
_reflns_number_gt                8768
_reflns_number_total             9523
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_refine_diff_density_max         2.1896
_refine_diff_density_min         -0.5229
_refine_diff_density_rms         0.0966
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.038(8)
_refine_ls_d_res_high            0.7744
_refine_ls_d_res_low             12.0218
_refine_ls_goodness_of_fit_ref   1.0686
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    106
_refine_ls_number_parameters     499
_refine_ls_number_reflns         9523
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.0685
_refine_ls_shift/su_max          0.1049
_refine_ls_shift/su_mean         0.0035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+6.0120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1119
_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. Restrained distances
 C41-C40
 0.009 with sigma of 1.54
 C19-C20
 1.54 with sigma of 0.009
3. Others
 Sof(Br2)=1-Sof(Br2A)=1-Sof(Br2A)=Sof(H30)
 Sof(Br1)=1-Sof(Br1A)=1-Sof(Br1A)=Sof(H9)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C5(H5a,H5b), C13(H13a,H13b), C14(H14a,H14b), C15(H15a,H15b),
 C17(H17a,H17b), C18(H18a,H18b), C19(H19a,H19b), C23(H23a,H23b), C26(H26a,H26b),
  C34(H34a,H34b), C35(H35a,H35b), C36(H36a,H36b), C38(H38a,H38b), C39(H39a,
 H39b), C40(H40a,H40b)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C21(H21), C29(H29), C30(H30), C42(H42)
4.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C16(H16a,H16b,
 H16c), C20(H20a,H20b,H20c), C31(H31a,H31b,H31c), C32(H32a,H32b,H32c), C33(H33a,
 H33b,H33c), C37(H37a,H37b,H37c), C41(H41a,H41b,H41c)
;
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_refinement_flags_posn
_atom_site_disorder_group
Br1 Br 0.570337(19) 0.26851(2) 0.50769(2) 0.03762(12) Uani 0.963721 . 1
Br1A Br 0.4648(5) 0.0891(4) 0.46141(3) 0.017(3) Uani 0.036279 . 2
O1 O 0.43683(17) 0.46778(17) 0.3638(2) 0.0425(7) Uani 1.000000 . .
N1 N 0.24812(15) 0.20283(15) 0.30268(17) 0.0203(5) Uani 1.000000 . .
N2 N 0.37768(15) 0.21417(15) 0.37326(17) 0.0210(5) Uani 1.000000 . .
C1 C 0.1858(2) 0.17766(18) 0.2671(2) 0.0224(7) Uani 1.000000 . .
C2 C 0.1261(2) 0.24182(19) 0.2585(2) 0.0254(7) Uani 1.000000 . .
H2a H 0.1015(2) 0.23990(19) 0.1998(2) 0.0304(9) Uiso 1.000000 R .
H2b H 0.0864(2) 0.23595(19) 0.3046(2) 0.0304(9) Uiso 1.000000 R .
C3 C 0.1717(2) 0.3213(2) 0.2708(2) 0.0287(8) Uani 1.000000 . .
C4 C 0.24076(18) 0.29094(19) 0.3241(2) 0.0229(6) Uani 1.000000 . .
H4 H 0.22792(18) 0.29575(19) 0.3881(2) 0.0275(8) Uiso 1.000000 R .
C5 C 0.31648(19) 0.33461(19) 0.3086(2) 0.0240(7) Uani 1.000000 . .
H5a H 0.32915(19) 0.33333(19) 0.2450(2) 0.0289(8) Uiso 1.000000 R .
H5b H 0.31165(19) 0.39193(19) 0.3267(2) 0.0289(8) Uiso 1.000000 R .
C6 C 0.37876(18) 0.2954(2) 0.3597(2) 0.0234(6) Uani 1.000000 . .
C7 C 0.44271(19) 0.3282(2) 0.4001(2) 0.0253(7) Uani 1.000000 . .
C8 C 0.4799(2) 0.2627(2) 0.4411(2) 0.0282(7) Uani 1.000000 . .
H8 H 0.5253(2) 0.2659(2) 0.4750(2) 0.0339(9) Uiso 0.036279 R 2
C9 C 0.44000(18) 0.1946(2) 0.4239(2) 0.0251(7) Uani 1.000000 . .
H9 H 0.45291(18) 0.1418(2) 0.4437(2) 0.0301(8) Uiso 0.963721 R 1
C10 C 0.1696(2) 0.0930(2) 0.2392(3) 0.0333(8) Uani 1.000000 . .
H10a H 0.1250(10) 0.0727(6) 0.2712(14) 0.0500(13) Uiso 1.000000 GR .
H10b H 0.1593(16) 0.0918(3) 0.1758(4) 0.0500(13) Uiso 1.000000 GR .
H10c H 0.2139(7) 0.0588(4) 0.2523(17) 0.0500(13) Uiso 1.000000 GR .
C11 C 0.1259(2) 0.3854(2) 0.3200(3) 0.0419(10) Uani 1.000000 . .
H11a H 0.1087(15) 0.3634(7) 0.3766(10) 0.0629(15) Uiso 1.000000 GR .
H11b H 0.1580(6) 0.4330(8) 0.3304(19) 0.0629(15) Uiso 1.000000 GR .
H11c H 0.0815(10) 0.4010(14) 0.2846(10) 0.0629(15) Uiso 1.000000 GR .
C12 C 0.1946(2) 0.3530(2) 0.1794(3) 0.0423(10) Uani 1.000000 . .
H12a H 0.1485(2) 0.3650(18) 0.1451(8) 0.0635(15) Uiso 1.000000 GR .
H12b H 0.2250(16) 0.4024(11) 0.1860(3) 0.0635(15) Uiso 1.000000 GR .
H12c H 0.2248(15) 0.3118(8) 0.1487(9) 0.0635(15) Uiso 1.000000 GR .
C21 C 0.4670(2) 0.4121(2) 0.4012(2) 0.0299(8) Uani 1.000000 . .
H21 H 0.5113(2) 0.4244(2) 0.4348(2) 0.0359(9) Uiso 1.000000 R .
C13 C 0.30052(18) 0.08258(18) 0.4026(2) 0.0217(6) Uani 1.000000 . .
H13a H 0.34801(18) 0.05435(18) 0.4200(2) 0.0261(7) Uiso 1.000000 R .
H13b H 0.26687(18) 0.04204(18) 0.3744(2) 0.0261(7) Uiso 1.000000 R .
C14 C 0.26134(18) 0.11249(19) 0.4858(2) 0.0253(7) Uani 1.000000 . .
H14a H 0.28874(18) 0.16107(19) 0.5072(2) 0.0304(9) Uiso 1.000000 R .
H14b H 0.20874(18) 0.12930(19) 0.4705(2) 0.0304(9) Uiso 1.000000 R .
C15 C 0.2572(2) 0.0514(2) 0.5606(2) 0.0295(7) Uani 1.000000 . .
H15a H 0.2343(2) 0.0007(2) 0.5381(2) 0.0353(9) Uiso 1.000000 R .
H15b H 0.3097(2) 0.0388(2) 0.5806(2) 0.0353(9) Uiso 1.000000 R .
C16 C 0.2112(2) 0.0807(2) 0.6384(2) 0.0344(8) Uani 1.000000 . .
H16a H 0.1591(5) 0.0934(16) 0.6192(4) 0.0516(12) Uiso 1.000000 GR .
H16b H 0.2095(14) 0.0383(7) 0.6836(8) 0.0516(12) Uiso 1.000000 GR .
H16c H 0.2350(9) 0.1294(10) 0.6630(12) 0.0516(12) Uiso 1.000000 GR .
C17 C 0.3646(2) 0.11277(19) 0.2437(2) 0.0260(7) Uani 1.000000 . .
H17a H 0.3314(2) 0.06975(19) 0.2194(2) 0.0312(8) Uiso 1.000000 R .
H17b H 0.4122(2) 0.08641(19) 0.2639(2) 0.0312(8) Uiso 1.000000 R .
C18 C 0.3849(3) 0.1697(2) 0.1692(3) 0.0421(11) Uani 1.000000 . .
H18a H 0.3372(3) 0.1877(2) 0.1402(3) 0.0506(13) Uiso 1.000000 R .
H18b H 0.4101(3) 0.2181(2) 0.1943(3) 0.0506(13) Uiso 1.000000 R .
C19 C 0.4384(3) 0.1322(3) 0.0981(3) 0.0566(13) Uani 1.000000 D .
H19a H 0.4549(3) 0.1752(3) 0.0569(3) 0.0679(16) Uiso 1.000000 R .
H19b H 0.4846(3) 0.1103(3) 0.1272(3) 0.0679(16) Uiso 1.000000 R .
C20 C 0.4003(3) 0.0661(3) 0.0472(3) 0.0634(15) Uani 1.000000 D .
H20a H 0.4346(10) 0.0469(17) 0.0008(17) 0.095(2) Uiso 1.000000 GR .
H20b H 0.388(2) 0.0213(11) 0.0869(6) 0.095(2) Uiso 1.000000 GR .
H20c H 0.3532(13) 0.0869(7) 0.021(2) 0.095(2) Uiso 1.000000 GR .
B1 B 0.3223(2) 0.1505(2) 0.3294(2) 0.0198(7) Uani 1.000000 . .
Br2 Br 0.396724(18) 0.72443(2) 0.50117(2) 0.03736(12) Uani 0.968210 . 1
Br2A Br 0.2911(7) 0.8920(7) 0.44384(3) 0.042(4) Uani 0.031790 . 2
O2 O 0.25725(18) 0.52123(17) 0.3665(2) 0.0564(9) Uani 1.000000 . .
N3 N 0.06813(15) 0.77829(14) 0.30348(17) 0.0187(5) Uani 1.000000 . .
N4 N 0.19817(15) 0.77216(15) 0.37381(18) 0.0218(6) Uani 1.000000 . .
C22 C 0.0058(2) 0.8011(2) 0.2670(2) 0.0238(7) Uani 1.000000 . .
C23 C -0.0521(2) 0.7348(2) 0.2608(2) 0.0280(8) Uani 1.000000 . .
H23a H -0.0920(2) 0.7412(2) 0.3064(2) 0.0336(9) Uiso 1.000000 R .
H23b H -0.0766(2) 0.7343(2) 0.2020(2) 0.0336(9) Uiso 1.000000 R .
C24 C -0.0057(2) 0.6575(2) 0.2759(2) 0.0261(7) Uani 1.000000 . .
C25 C 0.06320(17) 0.69073(17) 0.3288(2) 0.0197(6) Uani 1.000000 . .
H25 H 0.05070(17) 0.68745(17) 0.3930(2) 0.0236(7) Uiso 1.000000 R .
C26 C 0.13965(18) 0.64890(18) 0.3136(2) 0.0238(7) Uani 1.000000 . .
H26a H 0.13641(18) 0.59190(18) 0.3334(2) 0.0285(8) Uiso 1.000000 R .
H26b H 0.15184(18) 0.64910(18) 0.2499(2) 0.0285(8) Uiso 1.000000 R .
C27 C 0.20122(18) 0.69124(19) 0.3632(2) 0.0240(6) Uani 1.000000 . .
C28 C 0.26692(19) 0.6596(2) 0.4021(2) 0.0290(7) Uani 1.000000 . .
C29 C 0.30393(19) 0.7278(2) 0.4390(2) 0.0271(7) Uani 1.000000 . .
H29 H 0.35059(19) 0.7268(2) 0.4708(2) 0.0326(9) Uiso 0.031790 R 2
C30 C 0.26185(19) 0.7950(2) 0.4213(2) 0.0261(7) Uani 1.000000 . .
H30 H 0.27418(19) 0.8486(2) 0.4387(2) 0.0314(8) Uiso 0.968210 R 1
C31 C -0.0120(2) 0.8840(2) 0.2346(3) 0.0349(9) Uani 1.000000 . .
H31a H 0.0314(7) 0.9198(5) 0.2464(17) 0.0524(13) Uiso 1.000000 GR .
H31b H -0.0218(16) 0.8821(4) 0.1711(4) 0.0524(13) Uiso 1.000000 GR .
H31c H -0.0574(10) 0.9045(7) 0.2651(14) 0.0524(13) Uiso 1.000000 GR .
C32 C 0.0180(2) 0.6227(2) 0.1862(3) 0.0371(9) Uani 1.000000 . .
H32a H 0.0491(15) 0.5740(11) 0.1952(3) 0.0557(14) Uiso 1.000000 GR .
H32b H -0.0277(2) 0.6086(17) 0.1523(8) 0.0557(14) Uiso 1.000000 GR .
H32c H 0.0478(15) 0.6631(7) 0.1538(9) 0.0557(14) Uiso 1.000000 GR .
C33 C -0.0490(2) 0.5934(2) 0.3290(3) 0.0394(10) Uani 1.000000 . .
H33a H -0.0648(15) 0.6164(6) 0.3857(9) 0.0592(14) Uiso 1.000000 GR .
H33b H -0.0943(10) 0.5762(14) 0.2960(9) 0.0592(14) Uiso 1.000000 GR .
H33c H -0.0158(6) 0.5467(8) 0.3393(18) 0.0592(14) Uiso 1.000000 GR .
C42 C 0.2908(2) 0.5760(2) 0.4028(3) 0.0414(10) Uani 1.000000 . .
H42 H 0.3361(2) 0.5630(2) 0.4342(3) 0.0497(12) Uiso 1.000000 R .
C34 C 0.11489(19) 0.90114(18) 0.4022(2) 0.0235(7) Uani 1.000000 . .
H34a H 0.07218(19) 0.93258(18) 0.3767(2) 0.0282(8) Uiso 1.000000 R .
H34b H 0.15799(19) 0.93903(18) 0.4109(2) 0.0282(8) Uiso 1.000000 R .
C35 C 0.08998(17) 0.87030(17) 0.4922(2) 0.0231(6) Uani 1.000000 . .
H35a H 0.05465(17) 0.82425(17) 0.4834(2) 0.0277(8) Uiso 1.000000 R .
H35b H 0.13548(17) 0.84946(17) 0.5235(2) 0.0277(8) Uiso 1.000000 R .
C36 C 0.0514(3) 0.9318(2) 0.5501(2) 0.0362(9) Uani 1.000000 . .
H36a H 0.0846(3) 0.9802(2) 0.5536(2) 0.0435(11) Uiso 1.000000 R .
H36b H 0.0032(3) 0.9485(2) 0.5212(2) 0.0435(11) Uiso 1.000000 R .
C37 C 0.0333(2) 0.9053(2) 0.6415(2) 0.0315(8) Uani 1.000000 . .
H37a H 0.0090(14) 0.8519(8) 0.6398(3) 0.0473(12) Uiso 1.000000 GR .
H37b H 0.0805(3) 0.9022(16) 0.6760(5) 0.0473(12) Uiso 1.000000 GR .
H37c H -0.0015(13) 0.9443(9) 0.6688(7) 0.0473(12) Uiso 1.000000 GR .
C38 C 0.1819(2) 0.8713(2) 0.2445(3) 0.0324(8) Uani 1.000000 . .
H38a H 0.2278(2) 0.9014(2) 0.2640(3) 0.0389(10) Uiso 1.000000 R .
H38b H 0.1467(2) 0.9110(2) 0.2173(3) 0.0389(10) Uiso 1.000000 R .
C39 C 0.2061(3) 0.8108(3) 0.1737(3) 0.0580(16) Uani 1.000000 . .
H39a H 0.2320(3) 0.7645(3) 0.2023(3) 0.0696(19) Uiso 1.000000 R .
H39b H 0.1599(3) 0.7899(3) 0.1438(3) 0.0696(19) Uiso 1.000000 R .
C40 C 0.2610(4) 0.8485(4) 0.1030(3) 0.0672(16) Uani 1.000000 D .
H40a H 0.3038(4) 0.8765(4) 0.1326(3) 0.0806(19) Uiso 1.000000 R .
H40b H 0.2823(4) 0.8052(4) 0.0653(3) 0.0806(19) Uiso 1.000000 R .
C41 C 0.2199(4) 0.9033(5) 0.0517(4) 0.091(2) Uani 1.000000 D .
H41a H 0.1742(17) 0.8768(11) 0.028(3) 0.136(4) Uiso 1.000000 GR .
H41b H 0.205(3) 0.9497(16) 0.0880(9) 0.136(4) Uiso 1.000000 GR .
H41c H 0.2519(11) 0.922(3) 0.003(2) 0.136(4) Uiso 1.000000 GR .
B2 B 0.1408(2) 0.8339(2) 0.3308(2) 0.0202(7) Uani 1.000000 . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C8 1.882(3) .
Br1A C9 1.885(8) .
O1 C21 1.203(5) .
N1 C1 1.286(4) .
N1 C4 1.497(4) .
N1 B1 1.613(4) .
N2 C6 1.357(4) .
N2 C9 1.374(4) .
N2 B1 1.579(4) .
C1 C2 1.496(5) .
C1 C10 1.489(4) .
C2 H2a 0.9900 .
C2 H2b 0.9900 .
C2 C3 1.549(4) .
C3 C4 1.539(5) .
C3 C11 1.524(5) .
C3 C12 1.537(5) .
C4 H4 1.0000 .
C4 C5 1.529(4) .
C5 H5a 0.9900 .
C5 H5b 0.9900 .
C5 C6 1.488(5) .
C6 C7 1.388(4) .
C7 C8 1.407(5) .
C7 C21 1.451(5) .
C8 H8 0.9500 .
C8 C9 1.350(5) .
C9 H9 0.9500 .
C10 H10a 0.9800 .
C10 H10b 0.9800 .
C10 H10c 0.9800 .
C11 H11a 0.9800 .
C11 H11b 0.9800 .
C11 H11c 0.9800 .
C12 H12a 0.9800 .
C12 H12b 0.9800 .
C12 H12c 0.9800 .
C21 H21 0.9500 .
C13 H13a 0.9900 .
C13 H13b 0.9900 .
C13 C14 1.520(4) .
C13 B1 1.625(4) .
C14 H14a 0.9900 .
C14 H14b 0.9900 .
C14 C15 1.521(4) .
C15 H15a 0.9900 .
C15 H15b 0.9900 .
C15 C16 1.510(5) .
C16 H16a 0.9800 .
C16 H16b 0.9800 .
C16 H16c 0.9800 .
C17 H17a 0.9900 .
C17 H17b 0.9900 .
C17 C18 1.513(5) .
C17 B1 1.621(5) .
C18 H18a 0.9900 .
C18 H18b 0.9900 .
C18 C19 1.557(6) .
C19 H19a 0.9900 .
C19 H19b 0.9900 .
C19 C20 1.496(6) .
C20 H20a 0.9800 .
C20 H20b 0.9800 .
C20 H20c 0.9800 .
Br2 C29 1.881(3) .
Br2A C30 1.717(11) .
O2 C42 1.212(5) .
N3 C22 1.281(4) .
N3 C25 1.500(4) .
N3 B2 1.624(4) .
N4 C27 1.348(4) .
N4 C30 1.381(4) .
N4 B2 1.575(4) .
C22 C23 1.495(5) .
C22 C31 1.489(5) .
C23 H23a 0.9900 .
C23 H23b 0.9900 .
C23 C24 1.532(5) .
C24 C25 1.550(4) .
C24 C32 1.536(5) .
C24 C33 1.532(5) .
C25 H25 1.0000 .
C25 C26 1.525(4) .
C26 H26a 0.9900 .
C26 H26b 0.9900 .
C26 C27 1.490(4) .
C27 C28 1.395(5) .
C28 C29 1.415(5) .
C28 C42 1.444(5) .
C29 H29 0.9500 .
C29 C30 1.359(5) .
C30 H30 0.9500 .
C31 H31a 0.9800 .
C31 H31b 0.9800 .
C31 H31c 0.9800 .
C32 H32a 0.9800 .
C32 H32b 0.9800 .
C32 H32c 0.9800 .
C33 H33a 0.9800 .
C33 H33b 0.9800 .
C33 H33c 0.9800 .
C42 H42 0.9500 .
C34 H34a 0.9900 .
C34 H34b 0.9900 .
C34 C35 1.521(5) .
C34 B2 1.617(4) .
C35 H35a 0.9900 .
C35 H35b 0.9900 .
C35 C36 1.504(5) .
C36 H36a 0.9900 .
C36 H36b 0.9900 .
C36 C37 1.489(5) .
C37 H37a 0.9800 .
C37 H37b 0.9800 .
C37 H37c 0.9800 .
C38 H38a 0.9900 .
C38 H38b 0.9900 .
C38 C39 1.528(5) .
C38 B2 1.617(5) .
C39 H39a 0.9900 .
C39 H39b 0.9900 .
C39 C40 1.570(7) .
C40 H40a 0.9900 .
C40 H40b 0.9900 .
C40 C41 1.395(9) .
C41 H41a 0.9800 .
C41 H41b 0.9800 .
C41 H41c 0.9800 .

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
C4 N1 C1 109.4(3) . .
B1 N1 C1 128.0(3) . .
B1 N1 C4 122.4(2) . .
C9 N2 C6 107.8(3) . .
B1 N2 C6 127.1(3) . .
B1 N2 C9 124.6(3) . .
C2 C1 N1 113.7(3) . .
C10 C1 N1 125.8(3) . .
C10 C1 C2 120.5(3) . .
H2a C2 C1 111.11(18) . .
H2b C2 C1 111.11(19) . .
H2b C2 H2a 109.1 . .
C3 C2 C1 103.2(3) . .
C3 C2 H2a 111.11(18) . .
C3 C2 H2b 111.1(2) . .
C4 C3 C2 101.1(3) . .
C11 C3 C2 112.1(3) . .
C11 C3 C4 112.5(3) . .
C12 C3 C2 108.3(3) . .
C12 C3 C4 112.4(3) . .
C12 C3 C11 110.0(3) . .
C3 C4 N1 105.7(3) . .
H4 C4 N1 107.90(16) . .
H4 C4 C3 107.90(19) . .
C5 C4 N1 110.5(3) . .
C5 C4 C3 116.6(3) . .
C5 C4 H4 107.90(18) . .
H5a C5 C4 109.55(18) . .
H5b C5 C4 109.55(17) . .
H5b C5 H5a 108.1 . .
C6 C5 C4 110.5(3) . .
C6 C5 H5a 109.55(19) . .
C6 C5 H5b 109.55(17) . .
C5 C6 N2 120.0(3) . .
C7 C6 N2 109.3(3) . .
C7 C6 C5 130.7(3) . .
C8 C7 C6 105.5(3) . .
C21 C7 C6 128.0(3) . .
C21 C7 C8 126.4(3) . .
C9 C8 C7 108.4(3) . .
C8 C9 N2 108.9(3) . .
H10a C10 C1 109.5 . .
H10b C10 C1 109.5 . .
H10b C10 H10a 109.5 . .
H10c C10 C1 109.5 . .
H10c C10 H10a 109.5 . .
H10c C10 H10b 109.5 . .
H11a C11 C3 109.5 . .
H11b C11 C3 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C3 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
H12a C12 C3 109.5 . .
H12b C12 C3 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C3 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
C7 C21 O1 126.6(3) . .
H21 C21 O1 116.7(2) . .
H21 C21 C7 116.7(2) . .
H13b C13 H13a 107.3 . .
C14 C13 H13a 108.11(17) . .
C14 C13 H13b 108.11(17) . .
B1 C13 H13a 108.11(17) . .
B1 C13 H13b 108.11(17) . .
B1 C13 C14 116.7(3) . .
H14a C14 C13 108.48(17) . .
H14b C14 C13 108.48(17) . .
H14b C14 H14a 107.5 . .
C15 C14 C13 115.2(3) . .
C15 C14 H14a 108.48(18) . .
C15 C14 H14b 108.48(19) . .
H15a C15 C14 108.91(18) . .
H15b C15 C14 108.91(19) . .
H15b C15 H15a 107.7 . .
C16 C15 C14 113.3(3) . .
C16 C15 H15a 108.9(2) . .
C16 C15 H15b 108.9(2) . .
H16a C16 C15 109.5 . .
H16b C16 C15 109.5 . .
H16b C16 H16a 109.5 . .
H16c C16 C15 109.5 . .
H16c C16 H16a 109.5 . .
H16c C16 H16b 109.5 . .
H17b C17 H17a 107.2 . .
C18 C17 H17a 107.8(2) . .
C18 C17 H17b 107.8(2) . .
B1 C17 H17a 107.83(17) . .
B1 C17 H17b 107.83(18) . .
B1 C17 C18 117.9(3) . .
H18a C18 C17 108.7(2) . .
H18b C18 C17 108.7(2) . .
H18b C18 H18a 107.6 . .
C19 C18 C17 114.4(3) . .
C19 C18 H18a 108.7(3) . .
C19 C18 H18b 108.7(2) . .
H19a C19 C18 109.1(2) . .
H19b C19 C18 109.1(3) . .
H19b C19 H19a 107.9 . .
C20 C19 C18 112.3(4) . .
C20 C19 H19a 109.1(3) . .
C20 C19 H19b 109.1(3) . .
H20a C20 C19 109.5 . .
H20b C20 C19 109.5 . .
H20b C20 H20a 109.5 . .
H20c C20 C19 109.5 . .
H20c C20 H20a 109.5 . .
H20c C20 H20b 109.5 . .
N2 B1 N1 104.1(2) . .
C13 B1 N1 110.7(3) . .
C13 B1 N2 108.4(3) . .
C17 B1 N1 111.9(3) . .
C17 B1 N2 108.3(3) . .
C17 B1 C13 113.0(3) . .
C25 N3 C22 110.2(3) . .
B2 N3 C22 127.8(3) . .
B2 N3 C25 121.7(2) . .
C30 N4 C27 107.5(3) . .
B2 N4 C27 128.2(3) . .
B2 N4 C30 123.7(3) . .
C23 C22 N3 113.0(3) . .
C31 C22 N3 126.3(3) . .
C31 C22 C23 120.7(3) . .
H23a C23 C22 110.96(19) . .
H23b C23 C22 110.96(18) . .
H23b C23 H23a 109.0 . .
C24 C23 C22 104.0(3) . .
C24 C23 H23a 111.0(2) . .
C24 C23 H23b 110.96(18) . .
C25 C24 C23 101.2(2) . .
C32 C24 C23 108.8(3) . .
C32 C24 C25 112.4(3) . .
C33 C24 C23 113.1(3) . .
C33 C24 C25 111.0(3) . .
C33 C24 C32 110.0(3) . .
C24 C25 N3 104.7(2) . .
H25 C25 N3 108.34(16) . .
H25 C25 C24 108.34(18) . .
C26 C25 N3 110.4(2) . .
C26 C25 C24 116.4(3) . .
C26 C25 H25 108.34(18) . .
H26a C26 C25 109.60(16) . .
H26b C26 C25 109.60(18) . .
H26b C26 H26a 108.1 . .
C27 C26 C25 110.3(3) . .
C27 C26 H26a 109.60(18) . .
C27 C26 H26b 109.60(19) . .
C26 C27 N4 119.8(3) . .
C28 C27 N4 110.7(3) . .
C28 C27 C26 129.4(3) . .
C29 C28 C27 104.3(3) . .
C42 C28 C27 126.9(3) . .
C42 C28 C29 128.8(3) . .
C30 C29 C28 108.9(3) . .
C29 C30 N4 108.6(3) . .
H31a C31 C22 109.5 . .
H31b C31 C22 109.5 . .
H31b C31 H31a 109.5 . .
H31c C31 C22 109.5 . .
H31c C31 H31a 109.5 . .
H31c C31 H31b 109.5 . .
H32a C32 C24 109.5 . .
H32b C32 C24 109.5 . .
H32b C32 H32a 109.5 . .
H32c C32 C24 109.5 . .
H32c C32 H32a 109.5 . .
H32c C32 H32b 109.5 . .
H33a C33 C24 109.5 . .
H33b C33 C24 109.5 . .
H33b C33 H33a 109.5 . .
H33c C33 C24 109.5 . .
H33c C33 H33a 109.5 . .
H33c C33 H33b 109.5 . .
C28 C42 O2 124.9(4) . .
H42 C42 O2 117.6(2) . .
H42 C42 C28 117.6(2) . .
H34b C34 H34a 107.3 . .
C35 C34 H34a 108.08(17) . .
C35 C34 H34b 108.08(17) . .
B2 C34 H34a 108.08(18) . .
B2 C34 H34b 108.08(17) . .
B2 C34 C35 116.9(3) . .
H35a C35 C34 108.45(17) . .
H35b C35 C34 108.45(17) . .
H35b C35 H35a 107.5 . .
C36 C35 C34 115.3(3) . .
C36 C35 H35a 108.45(19) . .
C36 C35 H35b 108.5(2) . .
H36a C36 C35 108.24(19) . .
H36b C36 C35 108.2(2) . .
H36b C36 H36a 107.4 . .
C37 C36 C35 116.2(3) . .
C37 C36 H36a 108.2(2) . .
C37 C36 H36b 108.2(2) . .
H37a C37 C36 109.5 . .
H37b C37 C36 109.5 . .
H37b C37 H37a 109.5 . .
H37c C37 C36 109.5 . .
H37c C37 H37a 109.5 . .
H37c C37 H37b 109.5 . .
H38b C38 H38a 107.4 . .
C39 C38 H38a 108.2(3) . .
C39 C38 H38b 108.2(3) . .
B2 C38 H38a 108.22(19) . .
B2 C38 H38b 108.22(19) . .
B2 C38 C39 116.3(3) . .
H39a C39 C38 109.0(3) . .
H39b C39 C38 109.0(3) . .
H39b C39 H39a 107.8 . .
C40 C39 C38 113.0(3) . .
C40 C39 H39a 109.0(3) . .
C40 C39 H39b 109.0(3) . .
H40a C40 C39 109.9(3) . .
H40b C40 C39 109.9(3) . .
H40b C40 H40a 108.3 . .
C41 C40 C39 108.9(5) . .
C41 C40 H40a 109.9(4) . .
C41 C40 H40b 109.9(3) . .
H41a C41 C40 109.5 . .
H41b C41 C40 109.5 . .
H41b C41 H41a 109.5 . .
H41c C41 C40 109.5 . .
H41c C41 H41a 109.5 . .
H41c C41 H41b 109.5 . .
N4 B2 N3 103.8(2) . .
C34 B2 N3 109.9(3) . .
C34 B2 N4 110.3(3) . .
C38 B2 N3 111.0(3) . .
C38 B2 N4 107.4(3) . .
C38 B2 C34 113.9(3) . .

loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C19 C20 1 1.5400 0.0090 0.0443
C41 C40 1 0.0090 1.5400 -1.3857




_database_code_depnum_ccdc_archive 'CCDC 974411'
#===============================================================================
data_global
#===============================================================================
# 1. SUBMISSION DETAILS

_audit_creation_method           'APEX2 v2012.12-0'

_publ_requested_journal          'New Journal of Chemistry'

_publ_contact_author_name        'Jonathon S. Lindsey'
_publ_contact_author_address     
;
Department of Chemistry
NC State University
2620 Yarbrough Drive
Box 8204
Raleigh, NC 27695
;
_publ_contact_author_email       jlindsey@ncsu.edu
_publ_contact_author_fax         919-515-2830
_publ_contact_author_phone       919-515-6406



#===============================================================================

# 2. PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#===============================================================================


# 3. TITLE AND AUTHOR LIST
_publ_section_title              
;
Regioselective beta-Pyrrolic Electrophilic Substitution of Hydrodipyrrin-
Dialkylboron Complexes Facilitates Access to Synthetic Models for Chlorophyll f
;
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address

'Mengran Liu'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Marcin Ptaszek'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Olga Mass'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Daniel F. Minkler'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Roger D. Sommer'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jayeeta Bhaumik'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;
'Jonathan S. Lindsey'
;Department of Chemistry
North Carolina State University
Raleigh, NC 27695-8204
USA
;


#===============================================================================
# 4. TEXT
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;
#=============================================================================== 
data_x12094

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H39 B N2'
_chemical_formula_weight         402.41

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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'

_cell_length_a                   9.077(2)
_cell_length_b                   16.466(6)
_cell_length_c                   18.163(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.714(8)
_cell_angle_gamma                90.00
_cell_volume                     2555.6(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    8126
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      21.14
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Kappa Axis X8 Apex2'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54612
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         26.41
_reflns_number_total             5249
_reflns_number_gt                3293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SIR92
_computing_structure_refinement  XL
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1089P)²+0.9248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5249
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2220
_refine_ls_wR_factor_gt          0.1910
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4059(2) 0.13621(11) 0.20095(12) 0.0473(5) Uani 1 1 d . . .
N2 N 0.4236(2) 0.04273(11) 0.31409(12) 0.0498(5) Uani 1 1 d . . .
C1 C 0.3557(3) 0.18513(14) 0.14156(16) 0.0563(7) Uani 1 1 d . . .
C2 C 0.4824(3) 0.21461(16) 0.11428(16) 0.0634(7) Uani 1 1 d . . .
H2A H 0.4852 0.2747 0.1141 0.076 Uiso 1 1 calc R . .
H2B H 0.4671 0.1947 0.0608 0.076 Uiso 1 1 calc R . .
C3 C 0.6332(3) 0.18042(16) 0.17246(16) 0.0608(7) Uani 1 1 d . . .
C4 C 0.5702(3) 0.12431(13) 0.22116(13) 0.0451(5) Uani 1 1 d . . .
C5 C 0.6479(3) 0.07117(13) 0.27565(13) 0.0439(5) Uani 1 1 d . . .
H5 H 0.7561 0.0630 0.2844 0.053 Uiso 1 1 calc R . .
C6 C 0.5762(3) 0.02564(13) 0.32179(13) 0.0434(5) Uani 1 1 d . . .
C7 C 0.6368(3) -0.03097(13) 0.38142(13) 0.0435(5) Uani 1 1 d . . .
C8 C 0.5155(3) -0.04754(14) 0.41127(16) 0.0532(6) Uani 1 1 d . . .
H8 H 0.5208 -0.0834 0.4530 0.064 Uiso 1 1 calc R . .
C9 C 0.3886(3) -0.00243(15) 0.36906(16) 0.0581(7) Uani 1 1 d . . .
H9 H 0.2903 -0.0025 0.3769 0.070 Uiso 1 1 calc R . .
C10 C 0.1908(3) 0.20973(18) 0.1021(2) 0.0798(9) Uani 1 1 d . . .
H10A H 0.1590 0.1959 0.0464 0.120 Uiso 1 1 calc R . .
H10B H 0.1807 0.2684 0.1079 0.120 Uiso 1 1 calc R . .
H10C H 0.1235 0.1811 0.1259 0.120 Uiso 1 1 calc R . .
C11 C 0.7259(5) 0.2492(2) 0.2254(2) 0.1160(16) Uani 1 1 d . . .
H11A H 0.8188 0.2265 0.2652 0.174 Uiso 1 1 calc R . .
H11B H 0.6597 0.2759 0.2511 0.174 Uiso 1 1 calc R . .
H11C H 0.7583 0.2889 0.1937 0.174 Uiso 1 1 calc R . .
C12 C 0.7300(5) 0.1355(3) 0.1333(2) 0.1217(17) Uani 1 1 d . . .
H12A H 0.8215 0.1118 0.1731 0.183 Uiso 1 1 calc R . .
H12B H 0.7646 0.1732 0.1007 0.183 Uiso 1 1 calc R . .
H12C H 0.6671 0.0922 0.1005 0.183 Uiso 1 1 calc R . .
B1 B 0.3018(3) 0.09448(18) 0.2492(2) 0.0568(7) Uani 1 1 d . . .
C13 C 0.2276(3) 0.16461(17) 0.28810(19) 0.0698(8) Uani 1 1 d . . .
H13A H 0.1324 0.1854 0.2474 0.084 Uiso 1 1 calc R . .
H13B H 0.1939 0.1392 0.3292 0.084 Uiso 1 1 calc R . .
C14 C 0.3311(3) 0.23688(18) 0.32426(19) 0.0726(8) Uani 1 1 d . . .
H14A H 0.4283 0.2166 0.3639 0.087 Uiso 1 1 calc R . .
H14B H 0.3609 0.2645 0.2830 0.087 Uiso 1 1 calc R . .
C15 C 0.2568(4) 0.2985(2) 0.3625(2) 0.0927(11) Uani 1 1 d . . .
H15A H 0.1545 0.3149 0.3244 0.111 Uiso 1 1 calc R . .
H15B H 0.2366 0.2723 0.4073 0.111 Uiso 1 1 calc R . .
C16 C 0.3530(5) 0.3732(2) 0.3912(2) 0.1128(13) Uani 1 1 d . . .
H16A H 0.4570 0.3576 0.4266 0.169 Uiso 1 1 calc R . .
H16B H 0.3016 0.4077 0.4192 0.169 Uiso 1 1 calc R . .
H16C H 0.3634 0.4031 0.3466 0.169 Uiso 1 1 calc R . .
C17 C 0.1742(3) 0.03376(17) 0.19343(19) 0.0706(8) Uani 1 1 d . . .
H17A H 0.1209 0.0054 0.2254 0.085 Uiso 1 1 calc R . .
H17B H 0.0944 0.0665 0.1539 0.085 Uiso 1 1 calc R . .
C18 C 0.2359(4) -0.0286(2) 0.1517(2) 0.0860(10) Uani 1 1 d . . .
H18A H 0.3251 -0.0570 0.1902 0.103 Uiso 1 1 calc R . .
H18B H 0.2758 -0.0010 0.1138 0.103 Uiso 1 1 calc R . .
C19 C 0.1138(5) -0.0916(2) 0.1081(3) 0.1236(16) Uani 1 1 d . . .
H19A H 0.0733 -0.1187 0.1460 0.148 Uiso 1 1 calc R . .
H19B H 0.0251 -0.0631 0.0695 0.148 Uiso 1 1 calc R . .
C20 C 0.1694(7) -0.1504(4) 0.0695(4) 0.185(3) Uani 1 1 d . . .
H20A H 0.1965 -0.1251 0.0269 0.278 Uiso 1 1 calc R . .
H20B H 0.0883 -0.1915 0.0479 0.278 Uiso 1 1 calc R . .
H20C H 0.2626 -0.1760 0.1063 0.278 Uiso 1 1 calc R . .
C21 C 0.7952(3) -0.06491(12) 0.41117(13) 0.0423(5) Uani 1 1 d . . .
C22 C 0.8629(3) -0.08538(13) 0.49014(13) 0.0465(6) Uani 1 1 d . . .
H22 H 0.8043 -0.0775 0.5241 0.056 Uiso 1 1 calc R . .
C23 C 1.0115(3) -0.11657(13) 0.52004(14) 0.0497(6) Uani 1 1 d . . .
H23 H 1.0528 -0.1303 0.5739 0.060 Uiso 1 1 calc R . .
C24 C 1.1029(3) -0.12850(13) 0.47302(14) 0.0485(6) Uani 1 1 d . . .
C25 C 1.0369(3) -0.10965(13) 0.39446(14) 0.0491(6) Uani 1 1 d . . .
H25 H 1.0961 -0.1179 0.3608 0.059 Uiso 1 1 calc R . .
C26 C 0.8862(3) -0.07904(13) 0.36373(13) 0.0472(6) Uani 1 1 d . . .
H26 H 0.8439 -0.0674 0.3094 0.057 Uiso 1 1 calc R . .
C27 C 1.2681(3) -0.15867(16) 0.50705(17) 0.0639(7) Uani 1 1 d . . .
H27A H 1.3373 -0.1134 0.5315 0.096 Uiso 1 1 calc R . .
H27B H 1.3009 -0.1820 0.4654 0.096 Uiso 1 1 calc R . .
H27C H 1.2739 -0.2004 0.5464 0.096 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C1 1.299(3) . ?
N1 C4 1.424(3) . ?
N1 B1 1.641(3) . ?
N2 C9 1.366(3) . ?
N2 C6 1.373(3) . ?
N2 B1 1.568(4) . ?
C1 C2 1.479(4) . ?
C1 C10 1.481(4) . ?
C2 C3 1.527(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C12 1.499(4) . ?
C3 C4 1.518(3) . ?
C3 C11 1.540(5) . ?
C4 C5 1.331(3) . ?
C5 C6 1.434(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C7 C8 1.408(3) . ?
C7 C21 1.466(3) . ?
C8 C9 1.367(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
B1 C17 1.605(4) . ?
B1 C13 1.614(4) . ?
C13 C14 1.521(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.512(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.496(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.493(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.528(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.386(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.398(3) . ?
C21 C26 1.400(3) . ?
C22 C23 1.373(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 C27 1.500(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C1 N1 C4 110.0(2) . . ?
C1 N1 B1 126.8(2) . . ?
C4 N1 B1 123.12(19) . . ?
C9 N2 C6 106.8(2) . . ?
C9 N2 B1 124.5(2) . . ?
C6 N2 B1 128.26(19) . . ?
N1 C1 C2 112.8(2) . . ?
N1 C1 C10 125.8(3) . . ?
C2 C1 C10 121.4(2) . . ?
C1 C2 C3 105.3(2) . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C12 C3 C4 111.9(2) . . ?
C12 C3 C2 112.7(3) . . ?
C4 C3 C2 101.6(2) . . ?
C12 C3 C11 112.0(3) . . ?
C4 C3 C11 108.5(2) . . ?
C2 C3 C11 109.6(3) . . ?
C5 C4 N1 121.9(2) . . ?
C5 C4 C3 128.6(2) . . ?
N1 C4 C3 109.49(19) . . ?
C4 C5 C6 123.2(2) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
N2 C6 C7 109.63(19) . . ?
N2 C6 C5 118.3(2) . . ?
C7 C6 C5 131.8(2) . . ?
C6 C7 C8 105.9(2) . . ?
C6 C7 C21 128.47(19) . . ?
C8 C7 C21 125.6(2) . . ?
C9 C8 C7 107.4(2) . . ?
C9 C8 H8 126.3 . . ?
C7 C8 H8 126.3 . . ?
N2 C9 C8 110.3(2) . . ?
N2 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 B1 C17 108.2(2) . . ?
N2 B1 C13 110.6(2) . . ?
C17 B1 C13 113.8(2) . . ?
N2 B1 N1 103.99(18) . . ?
C17 B1 N1 110.3(2) . . ?
C13 B1 N1 109.5(2) . . ?
C14 C13 B1 117.4(2) . . ?
C14 C13 H13A 107.9 . . ?
B1 C13 H13A 107.9 . . ?
C14 C13 H13B 107.9 . . ?
B1 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
C15 C14 C13 114.7(3) . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 114.4(3) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 B1 115.8(2) . . ?
C18 C17 H17A 108.3 . . ?
B1 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
B1 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 C19 113.5(3) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 114.3(4) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 116.4(2) . . ?
C22 C21 C7 120.5(2) . . ?
C26 C21 C7 123.1(2) . . ?
C23 C22 C21 121.9(2) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 117.4(2) . . ?
C25 C24 C27 121.6(2) . . ?
C23 C24 C27 120.9(2) . . ?
C24 C25 C26 121.5(2) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 121.3(2) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -1.2(3) . . . . ?
B1 N1 C1 C2 177.3(2) . . . . ?
C4 N1 C1 C10 177.8(3) . . . . ?
B1 N1 C1 C10 -3.8(4) . . . . ?
N1 C1 C2 C3 -4.5(3) . . . . ?
C10 C1 C2 C3 176.5(3) . . . . ?
C1 C2 C3 C12 127.5(3) . . . . ?
C1 C2 C3 C4 7.6(3) . . . . ?
C1 C2 C3 C11 -107.1(3) . . . . ?
C1 N1 C4 C5 -173.9(2) . . . . ?
B1 N1 C4 C5 7.5(3) . . . . ?
C1 N1 C4 C3 6.5(3) . . . . ?
B1 N1 C4 C3 -172.0(2) . . . . ?
C12 C3 C4 C5 51.4(4) . . . . ?
C2 C3 C4 C5 171.9(2) . . . . ?
C11 C3 C4 C5 -72.7(4) . . . . ?
C12 C3 C4 N1 -129.1(3) . . . . ?
C2 C3 C4 N1 -8.7(3) . . . . ?
C11 C3 C4 N1 106.8(3) . . . . ?
N1 C4 C5 C6 -4.1(4) . . . . ?
C3 C4 C5 C6 175.3(2) . . . . ?
C9 N2 C6 C7 0.5(3) . . . . ?
B1 N2 C6 C7 -172.2(2) . . . . ?
C9 N2 C6 C5 -174.1(2) . . . . ?
B1 N2 C6 C5 13.2(3) . . . . ?
C4 C5 C6 N2 -5.8(3) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
N2 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C8 172.8(2) . . . . ?
N2 C6 C7 C21 -178.2(2) . . . . ?
C5 C6 C7 C21 -4.6(4) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C21 C7 C8 C9 178.3(2) . . . . ?
C6 N2 C9 C8 0.0(3) . . . . ?
B1 N2 C9 C8 173.1(2) . . . . ?
C7 C8 C9 N2 -0.5(3) . . . . ?
C9 N2 B1 C17 -63.4(3) . . . . ?
C6 N2 B1 C17 108.1(3) . . . . ?
C9 N2 B1 C13 61.8(3) . . . . ?
C6 N2 B1 C13 -126.7(2) . . . . ?
C9 N2 B1 N1 179.4(2) . . . . ?
C6 N2 B1 N1 -9.1(3) . . . . ?
C1 N1 B1 N2 -179.6(2) . . . . ?
C4 N1 B1 N2 -1.3(3) . . . . ?
C1 N1 B1 C17 64.6(3) . . . . ?
C4 N1 B1 C17 -117.1(2) . . . . ?
C1 N1 B1 C13 -61.3(3) . . . . ?
C4 N1 B1 C13 117.0(2) . . . . ?
N2 B1 C13 C14 73.4(3) . . . . ?
C17 B1 C13 C14 -164.6(3) . . . . ?
N1 B1 C13 C14 -40.7(3) . . . . ?
B1 C13 C14 C15 -177.6(3) . . . . ?
C13 C14 C15 C16 -174.5(3) . . . . ?
N2 B1 C17 C18 -60.7(3) . . . . ?
C13 B1 C17 C18 175.9(3) . . . . ?
N1 B1 C17 C18 52.4(3) . . . . ?
B1 C17 C18 C19 172.4(3) . . . . ?
C17 C18 C19 C20 -179.5(5) . . . . ?
C6 C7 C21 C22 146.8(2) . . . . ?
C8 C7 C21 C22 -30.1(3) . . . . ?
C6 C7 C21 C26 -33.5(3) . . . . ?
C8 C7 C21 C26 149.6(2) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?
C7 C21 C22 C23 -179.4(2) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C25 -1.6(3) . . . . ?
C22 C23 C24 C27 176.9(2) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C27 C24 C25 C26 -177.7(2) . . . . ?
C24 C25 C26 C21 0.8(3) . . . . ?
C22 C21 C26 C25 -1.7(3) . . . . ?
C7 C21 C26 C25 178.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.046


_database_code_depnum_ccdc_archive 'CCDC 974412'
