Octaethyl-1,3-oxazinochlorin: A β-Octaethylchlorin Analogue Made by Pyrrole Expansion.
Meehan, Eileen; Li, Ruoshi; Zeller, Matthias; Brückner, Christian; Organic letters 17 (2015) 2210–2213; doi:10.1021/acs.orglett.5b00800

data_1520301
_publ_section_title
;
 Octaethyl-1,3-oxazinochlorin: A \b-Octaethylchlorin Analogue Made by
 Pyrrole Expansion.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2210
_journal_page_last               2213
_journal_paper_doi               10.1021/acs.orglett.5b00800
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C37 H49 N5 O, 0.666(C6 H14)'
_chemical_formula_sum            'C41 H58.333 N5 O'
_chemical_formula_weight         637.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.584(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.0651(12)
_cell_length_b                   15.2582(7)
_cell_length_c                   9.5468(5)
_cell_measurement_reflns_used    9647
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      66.6241
_cell_measurement_theta_min      3.3620
_cell_volume                     3771.8(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_collection       'Apex2 v2014.1-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_refinement
;  
SHELXL-2014/7 (Sheldrick, 2014), 
SHELXLE Rev656 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker AXS X8 Prospector CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_laue_measured_fraction_full 0.987
_diffrn_reflns_laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            49915
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         1.706
_diffrn_source                   'I-mu-S microsource X-ray tube'
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2014.1-0 (Bruker, 2014)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       plate
_exptl_crystal_F_000             1389
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     796
_refine_ls_number_reflns         6650
_refine_ls_number_restraints     1274
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0820P)^2^+0.7651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5350
_reflns_number_total             6650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00800_si_003.cif
_cod_data_source_block           Prosp15mz035_0m
_cod_database_code               1520301
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.763
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              97288
_shelx_hkl_checksum              23384